Sodium ethoxide → HCID 178494647, compound

HRID 2173924Notes

Reaction equation

[F:1][C:2]([F:42])([F:41])[C:3]([C:30]1[NH:34][C:33]2[CH:35]=[CH:36][C:37]([C:39]#[N:40])=[CH:38][C:32]=2[N:31]=1)([O:28][CH3:29])[C:4]1[C:12]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:11][C:10]([CH3:17])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2S(C1C=CC(C)=CC=1)(=O)=O.[O-]CC.[Na+]>CCO>[F:42][C:2]([F:1])([F:41])[C:3]([C:30]1[NH:34][C:33]2[CH:35]=[CH:36][C:37]([C:39]#[N:40])=[CH:38][C:32]=2[N:31]=1)([O:28][CH3:29])[C:4]1[C:12]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:11][C:10]([CH3:17])=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2

Participants

Conditions

Temperature: 60 °C

Procedure

To (±)-2-(2,2,2-trifluoro-1-methoxy-1-(7-methyl-5-(methylsulfonyl)-1-tosyl-1H-indol-4-yl)ethyl)-1H-benzo[d]imidazole-5-carbonitrile (172 mg, 0.279 mmol) in EtOH (2.8 mL) was added sodium ethoxide (21% in EtOH, 2 mL, 5.58 mmol) and the mixture was stirred at 60° C. After 45 minutes the reaction was cooled to room temperature and purified directly by flash chromatography (0-100% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.84-13.00 (m, 1H) 11.59 (br. s., 1H) 8.47 (m) 8.00-8.19 (m) 7.94 (m) 7.61-7.72 (m, 1H) 7.50-7.61 (m) 7.27 (br. s., 1H) 5.45 (br. s., 1H) 3.39 (br. s., 3H) 3.21 (br. s., 3H) 2.57 (s, 3H). HRMS calcd. for C21H17F3N4O3S (M+H)+ 463.1052. found 463.1031.

Workup

temperatureAfter 45 minutes the reaction was cooled to room temperature
custompurified directly by flash chromatography (0-100% EtOAc in heptanes)

Sources & evidence

ORD record: ord-a7dcf5453af646119e86907a3aac4ba6
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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