Cesium carbonate → 5-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethylsulfanyl]-benzofuran-2-carboxylic acid methyl ester

HRID 2215098Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][C:8]=2[CH:9]=1)=[O:4].Cl[CH2:16][C:17]1[S:21][C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[N:19][C:18]=1[CH3:32].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([S:14][CH2:16][C:17]3[S:21][C:20]([C:22]4[CH:23]=[CH:24][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:26][CH:27]=4)=[N:19][C:18]=3[CH3:32])=[CH:10][C:8]=2[CH:9]=1)=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5-mercapto-benzofuran-2-carboxylic acid methyl ester (300 mg, 1.4 mmol) and 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (550 mg, 1.9 mmol) was dissolved in 5 ml anhydrous acetonitrile followed by addition of cesium carbonate (700 mg, 2.1 mmol). The reaction was then stirred at 60° C. for 2 hours, filtered and concentrated in vacuo. Purification by flash column chromatography (gradient elution: 5% EtOAc/hexanes to 45% EtOAc/hexanes), gave the title compound (410 mg, 61%) as a pale yellow solid. M.p. 132–133° C.; IR (thin film) cm−1: 1173; 400 MHz 1H NMR (DMSO-d6) δ 7.95 (d, 2H, J=8.1 Hz), 7.79 (s, 1H), 7.74 (d, 2H, J=8.1 Hz), 7.65 (m, 2H), 7.51 (d, 1H, J=9.0 Hz), 4.44 (s, 2H), 3.82 (s, 3H); MS m/z 464 (M+1); Annl. Calc'd for C22H16F3N1O3S2 C, 57.01; H, 3.48; N, 3.02; found: C, 56.94; H, 3.44; N, 2.84.

Workup

filtrationfiltered
concentrationconcentrated in vacuo
customPurification
washby flash column chromatography (gradient elution: 5% EtOAc/hexanes to 45% EtOAc/hexanes)

Sources & evidence

ORD record: ord-e3b9207f673b4f3a846a9d5e64ff14c0
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109222B2

Reaction notes

Loading…