Sodium ethoxide → HCID 178422451, compound

HRID 2174035Notes

Reaction equation

[NH2:1][C:2]([C:28]1[NH:32][C:31]2[CH:33]=[CH:34][C:35]([C:37]#[N:38])=[CH:36][C:30]=2[N:29]=1)([C:7]1[C:15]([Br:16])=[CH:14][C:13]([CH3:17])=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2S(C1C=CC(C)=CC=1)(=O)=O)[C:3]([F:6])([F:5])[F:4].[O-]CC.[Na+]>CCO>[NH2:1][C:2]([C:28]1[NH:32][C:31]2[CH:33]=[CH:34][C:35]([C:37]#[N:38])=[CH:36][C:30]=2[N:29]=1)([C:7]1[C:15]([Br:16])=[CH:14][C:13]([CH3:17])=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)[C:3]([F:5])([F:4])[F:6]

Participants

Conditions

Temperature: 60 °C

Procedure

To (±)-2-(1-amino-1-(5-bromo-7-methyl-1-tosyl-1H-indol-4-yl)-2,2,2-trifluoroethyl)-1H-benzo[d]imidazole-5-carbonitrile (203 mg, 0.337 mmol) in EtOH (3.3 mL) was added sodium ethoxide (22% solution in EtOH) (2.5 mL, 6.74 mmol) and the mixture was stirred at 60° C. After 3 hours the reaction mixture was purified directly by flash chromatography (0-100% EtOAc in heptanes) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.61 (br. s., 1H) 11.37 (br. s., 1H) 8.25 (m) 7.94 (m) 7.83-7.90 (m) 7.51-7.61 (m) 7.33 (br. s., 1H) 7.16 (s, 1H) 6.92 (br. s., 1H) 3.22 (s, 2H) 2.46 (d, J=0.51 Hz, 3H). HRMS calcd. for C19H13BrF3N5 (M+H)+ 448.0379. found 448.0389.

Workup

customAfter 3 hours the reaction mixture was purified directly by flash chromatography (0-100% EtOAc in heptanes)

Sources & evidence

ORD record: ord-fa4f288191f04fa6a7914d492fe64154
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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