4-CHLORO-5-IODO-1-(TRIISOPROPYLSILYL)-1H-PYRROLO[2,3-B]PYRIDINE synthesis

7synthesis methods

Product Name:4-CHLORO-5-IODO-1-(TRIISOPROPYLSILYL)-1H-PYRROLO[2,3-B]PYRIDINE
CAS Number:1015609-83-2
Molecular formula:C16H24ClIN2Si
Molecular Weight:434.82

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-1-[tris(1-methylethyl)silyl]-

651744-48-8
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$225.00/1g

4-CHLORO-5-IODO-1-(TRIISOPROPYLSILYL)-1H-PYRROLO[2,3-B]PYRIDINE

1015609-83-2
15 suppliers
$155.00/50mg

Yield:1015609-83-2 53%

Reaction Conditions:

Stage #1: 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridinewith sec.-butyllithium in tetrahydrofuran at -78; for 1 h;
Stage #2: with iodine in tetrahydrofuran at -78 - 0; for 0.5 h;

Steps:

3.5 Synthesis of 5

53 ml of sec-BuLi are added dropwise over the course of 30 min to a solution of 11 g of intermediate 4 in 250 ml of THF at -78° C. After 1 h, 18 g of iodine are added dropwise over the course of 30 min. While the batch warms to 0° C., a suspension forms. The mixture is worked up using saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic phases are washed with water and saturated NaCL solution and dried over sodium sulfate, giving 5.25 g (53%) of the product 4-chloro-5-iodo-1-triisopropylsilanyl-1 H-pyrrolo[2,3-b]pyridine as colourless solid; LCMS: (method A) 435.0 (M+H), RT. 7.98 min, 96.9% (max). ¹H NMR 400 MHz, DMSO-d₆: δ [ppm] 8.52 (s, 1H), 7.57 (d, J=3.52 Hz, 1H), 6.67 (d, J=3.48 Hz, 1H), 1.80-1.88 (m, 3H), 1.04 (d, J=7.52 Hz, 18H).

References:

US2015/218155,2015,A1 Location in patent:Paragraph 0319; 0320

7553-56-2 Synthesis