5-Bromo-3-Isopropyl-1-(Toluene-4-Sulfonyl)-1H-Pyrrolo[2,3-B]Pyridine synthesis

4synthesis methods

Product Name:5-Bromo-3-Isopropyl-1-(Toluene-4-Sulfonyl)-1H-Pyrrolo[2,3-B]Pyridine
CAS Number:1620574-97-1
Molecular formula:C17H17BrN2O2S
Molecular Weight:393.3

1H-Pyrrolo[2,3-b]pyridine-3-methanol, 5-bromo-α,α-dimethyl-1-[(4-methylphenyl)sulfonyl]-

1620574-96-0
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5-Bromo-3-Isopropyl-1-(Toluene-4-Sulfonyl)-1H-Pyrrolo[2,3-B]Pyridine

1620574-97-1
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$561.00/1g

Yield:1620574-97-1 69%

Reaction Conditions:

with triethylsilane;trifluoroacetic acid in dichloromethane at 0 - 20;

Steps:

1.4 Step 4: 5-bromo-3-isopropyl-l-tosyl-lH-pyrrolo[2,3-b]pyridine

To a solution of 2-(5-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-yl)propan-2-ol (50 g, 0.122 mol) in dry dichloromethane (1000 mL) was added dropwise triethylsilane (42.6 g, 0.366 mol) and trifluoroacetic acide (71 g, 0.623 mol) at 0 °C. The resulting mixture was warmed up to RT and stirred overnight. The mixture was poured into ice -water and basified with saturated sodium bicarbonate to pH 4 - 5 and extracted with dichloromethane (3 x 1000 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100- 200 mesh, 3% to 10% ethyl acetate in petroleum ether) affording 5-bromo-3-isopropyl-l-tosyl-lH-pyrrolo[2,3-b]pyridine (33.3 g, 69 %): NMR (400MHz, Chloroform-d), δ 8.409-8.415 (d, / = 2.4 Hz, 1H), 8.010-8.041 (m, 2H), 7.945-7.950 (d, / = 2 Hz, 1H), 7.454-7.456 (d, J = 0.8 Hz, 1H), 7.257-7.280 (m, 2H), 2.994-3.031 (m, 1H), 2.371 (s, 3H), 1.298-1.321 (dd, / = 6.8 Hz, 6H).

References:

WO2014/111496,2014,A1 Location in patent:Page/Page column 102

866545-96-2 Synthesis

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1620574-97-1
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References

1052633-38-1 Synthesis

Ethanone, 1-[5-broMo-1-[(4-Methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl]-

1052633-38-1
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1620574-97-1
8 suppliers
$561.00/1g

References

183208-35-7 Synthesis

183208-35-7
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1620574-97-1
8 suppliers
$561.00/1g

References