Tetrahydrofuran → HCID 67229384, compound

HRID 1515876Notes

Reaction equation

[C:1]([O:5][C:6](=[O:44])[NH:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([C:17]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=3)=[CH:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:14](S(C3C=CC=CC=3)(=O)=O)[C:11]2=[N:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:44])[NH:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([C:17]([C:25]3[CH:26]=[CH:27][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][CH:30]=3)=[CH:18][CH:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[NH:14][C:11]2=[N:12][CH:13]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of {1-benzenesulfonyl-2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-pyran-4-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-carbamic acid tert-butyl ester (670 mg, 1.05 mmol) and tetrabutylammonium fluoride in tetrahydrofuran (1 M, 21 mL, 21 mmol) was stirred for 3 h at 60° C. After cooling to room temperature, the mixture was poured into brine (20 mL), extracted with ethyl acetate (2×100 mL), washed with a saturated aqueous ammonium chloride solution (3×50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to give {2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-pyran-4-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-carbamic acid tert-butyl ester (0.52 g, 100%) which was used in the next step without purification: LC/MS m/e calcd for C26H31N3O5S [M+H]+ 498.62, observed 498.2.

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate (2×100 mL)
washwashed with a saturated aqueous ammonium chloride solution (3×50 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e74cfa89a69b4bd1b0dbffbb94701cae
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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