Tetrabutylammonium Fluoride → 2-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-but-1-enyl]-benzoic acid methyl ester

HRID 1515842Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:15]2[N:24](S(C3C=CC=CC=3)(=O)=O)[C:18]3=[N:19][CH:20]=[C:21]([F:23])[CH:22]=[C:17]3[CH:16]=2)=[CH:11][CH:12]([CH3:14])[CH3:13])=[CH:6][C:5]=1[F:34].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:15]2[NH:24][C:18]3=[N:19][CH:20]=[C:21]([F:23])[CH:22]=[C:17]3[CH:16]=2)=[CH:11][CH:12]([CH3:14])[CH3:13])=[CH:6][C:5]=1[F:34]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 4-[1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-but-1-enyl]-2-fluoro-benzoic acid methyl ester (2.50 g, 5 mmol) and tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 50 mL) was stirred at 25° C. for 40 h. The reaction was quenched with a saturated aqueous ammonium chloride solution (50 mL). The mixture was extracted with ethyl acetate (2×150 mL), washed with a saturated aqueous ammonium chloride solution (3×100 mL), brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-but-1-enyl]-benzoic acid methyl ester (660 mg, 36%) which was used in the next step without further purification: LC/MS m/e calcd for C20H18F2N2O2 [M+H]+ 357.38, observed 356.9.

Workup

customThe reaction was quenched with a saturated aqueous ammonium chloride solution (50 mL)
extractionThe mixture was extracted with ethyl acetate (2×150 mL)
washwashed with a saturated aqueous ammonium chloride solution (3×100 mL), brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e2fbd0b4301f430b82bdd40b17173285
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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