ChemicalBook CAS DataBase List 6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine

6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine synthesis

4synthesis methods

Product Name:6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine
CAS Number:1259512-11-2
Molecular formula:C9H11BrN2
Molecular Weight:227.1

1190862-33-9 Synthesis

6-bromo-3,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

1190862-33-9
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6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine

1259512-11-2
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Yield:1259512-11-2 100%

Reaction Conditions:

with sodium tetrahydroborate;boron trifluoride diethyl etherate in tetrahydrofuran at 0 - 20; for 6 h;Inert atmosphere;

Steps:

8.5 Step 5) 6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine

To a solution of 6-bromo-3,3-dimethyl-lH-pyrrolo[3,2-b]pyridin-2(3H)-one (1.21 g, 5 mmol) in THF (100 mL) was added NaBH₄ (0.95 g, 25 mmol), followed by the dropwise addition of BF3-Et₂0 (47%, 9.5 mL, 35 mmol) at 0 °C under ₂ atmosphere. The reaction was stirred at rt for 6 h, then quenched with saturated aqueous NH₄C1 (25 mL). The resulted mixture was continued to stirred at rt overnight, then diluted with H₂0 (100 mL) and extracted with EtOAc (100 mL x 3). The combined organic phases were dried over anhydrous Na₂S0₄ and concentrated in vacuo. The residue was purified by a silica gel column chromatography (100% DCM) to give the title compound as a yellow solid (1.46 g, 100%). MS (ESI, pos. ion) m/z: 227 [M + H]⁺.

References:

WO2014/89324,2014,A1 Location in patent:Paragraph 0218

3-Pyridinamine, 5-bromo-2-iodo-N-(2-methyl-2-propen-1-yl)-

1403901-48-3
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1259512-11-2
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References

methyl 2-(5-bromo-3-nitropyridin-2-yl)-2-methylpropanoate

1259512-10-1
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1259512-11-2
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References

13535-01-8 Synthesis

13535-01-8
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1259512-11-2
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References