Tetrabutylammonium Fluoride → HCID 53251717, compound

HRID 1515774Notes

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-1-(4-methanesulfonyl-phenyl)-3,3-dimethyl-butan-1-ol (190 mg, 0.37 mmol) and tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 3 mL) was stirred at 25° C. for 16 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 (3×25 mL), brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-[(E)-1-(4-methanesulfonyl-phenyl)-3,3-dimethyl-but-1-enyl]-1H-pyrrolo[2,3-b]pyridine (50 mg, 96%): LC/MS m/e calcd for C20H22N2O2S [M+H]+ 355.47, observed 355.3; 1H NMR (400 MHz, CD3OD) δ ppm 8.23 (d, J=7.6 Hz, 2H), 8.00-8.06 (m, J=8.1 Hz, 2H), 7.54-7.61 (m, J=8.1 Hz, 2H), 7.31-7.37 (m, 1H), 6.67 (s, 1H), 5.86 (s, 1H), 3.16-3.27 (s, 3H), 0.95-1.03 (s, 9H).

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 (3×25 mL), brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1f86f834f1084a2a8f83c98089f2e097
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

Loading…