Triethylamine → methanesulfonic acid 2-(2-cyano-1H-indol-5-yl)-2-phenyl-ethyl ester

HRID 268902Notes

Reaction equation

[OH:1][CH2:2][CH:3]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([C:19]#[N:20])=[CH:13]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(N(CC)CC)C>O1CCCC1>[C:19]([C:14]1[NH:15][C:16]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:2][O:1][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:18][CH:17]=2)#[N:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(2-hydroxy-1-phenyl-ethyl)-1H-indole-2-carbonitrile CCLXX (218 mg, 0.789 mmol) in tetrahydrofuran (10 mL) was added at 0° C. methanesulfonyl chloride (73 μL, 0.947 mmol) followed by triethylamine (0.16 mL, 1.183 mmol) and the resulting mixture was stirred at 0° C. for 3 hours. The precipitate which formed was filtered off and the filtrate was evaporated under reduced pressure. The crude residue was purified by flash chromatography to give 240 mg of methanesulfonic acid 2-(2-cyano-1H-indol-5-yl)-2-phenyl-ethyl ester CCLXXI.

Workup

customThe precipitate which formed
filtrationwas filtered off
customthe filtrate was evaporated under reduced pressure
customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record: ord-4dc1c7f95b574c7e92617c08f0dcd186
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446118B2

Reaction notes

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