Tetrabutylammonium Fluoride → HCID 67228309, compound

HRID 1515777Notes

Reaction equation

C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:19]([C:26]2[CH:31]=[CH:30][C:29]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:28][CH:27]=2)=[CH:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH:21]1([CH:20]=[C:19]([C:26]2[CH:27]=[CH:28][C:29]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:30][CH:31]=2)[C:11]2[NH:10][C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of N-{4-[1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-methanesulfonamide (150 mg, 0.28 mmol) and tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 3 ml) was stirred at 45° C. for 96 h. The reaction was quenched with a saturated aqueous ammonium chloride solution (20 mL). The mixture was extracted with ethyl acetate (2×50 mL), washed with a saturated aqueous ammonium chloride solution (3×50 mL), brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford N-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-phenyl}-methanesulfonamide (83 mg, 75%) as a white solid: LC/MS m/e calcd for C21H23N3O2S [M+H]+ 382.50, observed 382.0.

Workup

customThe reaction was quenched with a saturated aqueous ammonium chloride solution (20 mL)
extractionThe mixture was extracted with ethyl acetate (2×50 mL)
washwashed with a saturated aqueous ammonium chloride solution (3×50 mL), brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-67d4c71e5a154bae9fe9ebb7d612d85d
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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