2,2,2-Trifluoroethanol → Trifluoroethyl 8-bromo-6-phenyl-4H-benzo[f]imidazo [1,5-a][1,4]diazepine-3-carboxylate

HRID 75247Notes

Reaction equation

HRID 75247 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[K+].[Br-:8].C[Si](C#C[C:15]1[CH:16]=[CH:17][C:18]2[N:24]3[CH:25]=[N:26][C:27]([C:28](OCC)=[O:29])=[C:23]3[CH2:22][N:21]=[C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3F)[C:19]=2[CH:40]=1)(C)C>>[Br:8][C:15]1[CH:16]=[CH:17][C:18]2[N:24]3[CH:25]=[N:26][C:27]([C:28]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[O:29])=[C:23]3[CH2:22][N:21]=[C:20]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:19]=2[CH:40]=1

Participants

4

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 253877Potassium BromideHCID 21930951HCID 21930951, compound

Product 1

HCID 21065261Trifluoroethyl 8-bromo-6-phenyl-4H-benzo[f]imidazo [1,5-a][1,4]diazepine-3-carboxylate

Procedure

A white solid (69.1%) from acid 27 and 2,2,2-trifluoroethanol: mp 202-204° C.; IR (KBr) 3114, 1711, 1608, 1495, 1368, 1288, 1158 cm−1; 1H NMR (300 MHz, CDCl3) δ 4.10 (d, 1H, J=12.6 Hz), 4.68 (m, 1H), 4.85 (m, 1H), 6.02 (d, 1H, J=12.6 Hz), 7.41-7.54 (m, 6H), 7.62 (d, 1H, J=2.1 Hz), 7.83 (dd, 1H, J=2.1 Hz, 8.4 Hz), 7.97 (s, 1H); MS (EI) m/e (rel intensity) 463 (M+, 14), 465 (14).

Sources & evidence

ORD record
ord-f6b385861a2e44d99aa6d5532919db68
Source dataset
uspto-grants-2014_09
Patent number
US08835424B2

Reaction notes

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