Dimethylformamide → HCID 73014210, compound

HRID 2234652Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:5]2=[N:6][CH:7]=1.P(Cl)(Cl)(Cl)=O.CN(C)[CH:26]=[O:27]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:26]=[O:27])=[CH:9][N:8]([CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:15])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24813Phosphorus oxychloride

HCID 68691434HCID 68691434, compound

Product 1

HCID 73014210HCID 73014210, compoundYield 82%

Conditions

Temperature: 50 °C

Procedure

2,2-Dimethyl-propionic acid 5-bromo-pyrrolo[2,3-b]pyridin-1-ylmethyl ester (4.09 g, 13.14 mmol) was dissolved in N,N-dimethylformamide (4 ml), and phosphorus oxy-chloride (1.33 ml) was added. The reaction mixture was stirred for 18 hours at 50° C. The reaction was quenched with saturated, aqueous sodium bicarbonate, and the mixture was extracted with dichloromethane. The organic layer was dried over sodium sulfate, concentrated, and purified by flash chromatography (0-100% (ethyl acetate in hexanes) to give 3.65 g (82%) of 2,2-dimethyl-propionic acid 5-bromo-3-formyl-pyrrolo[2,3-b]pyridin-1-ylmethyl ester. MS: m/z 338.0+340.0 (M+H+).

Workup

customThe reaction was quenched with saturated, aqueous sodium bicarbonate
extractionthe mixture was extracted with dichloromethane
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated
custompurified by flash chromatography (0-100% (ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-d7240afd111142e5b8afd778ed73d8a4
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709645B2

Reaction notes

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