Dichloromethane → 685513-97-7

HRID 79514Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:3]=12.[Li]C(CC)C.Cl[C:27]([O:29][CH3:30])=[O:28].C(Cl)Cl>C1COCC1>[Cl:1][C:2]1[C:7]([C:27]([O:29][CH3:30])=[O:28])=[CH:6][N:5]=[C:4]2[N:8]([Si:11]([CH:15]([CH3:17])[CH3:16])([CH:18]([CH3:20])[CH3:19])[CH:12]([CH3:13])[CH3:14])[CH:9]=[CH:10][C:3]=12

Participants

Conditions

Temperature: -78 °C

Procedure

4-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (0.50 g, 1.612 mmol, see Example 1) was dissolved in THF (15 mL) and cooled to −78° C. s-BuLi (2.54 mL, 3.56 mmol) was then added dropwise, and the solution was stirred at −78° C. for 30 minutes. Methyl chloroformate (0.38 mL, 4.98 mmol) was then added as a THF (2 mL) solution, and the reaction was stirred for an additional 30 minutes. The reaction was then quenched with saturated NH4Cl and allowed to warm to room temperature. The reaction was then extracted with DCM (3×50 mL), dried, and filtered to give a crude residue. The crude residue was purified by column chromatography with 5:1 hexane:DCM to give methyl 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.55 g, 91% yield).

Workup

additionwas then added dropwise
stirringthe reaction was stirred for an additional 30 minutes
customThe reaction was then quenched with saturated NH4Cl
temperatureto warm to room temperature
extractionThe reaction was then extracted with DCM (3×50 mL)
customdried
filtrationfiltered
customto give a crude residue
customThe crude residue was purified by column chromatography with 5:1 hexane

Sources & evidence

ORD record: ord-7e555e64f1a341cda778dd344ade840f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841304B2

Reaction notes

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