Potassium Carbonate → HCID 68494938, compound

HRID 2381857Notes

Reaction equation

[CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13]([C:17]2[N:21]=[CH:20][NH:19][N:18]=2)=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1>CN(C)C=O>[CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13]([C:17]2[N:21]=[CH:20][N:19]([CH2:33][C:32]3[CH:35]=[CH:36][C:29]([F:28])=[CH:30][CH:31]=3)[N:18]=2)=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-benzyl-3-methyl-5-(1H-1,2,4-triazol-3-yl)thiophene-2-carboxamide (0.07 g, 0.22 mmol), potassium carbonate (0.03 g, 0.22 mmol) and 4-fluorobenzyl bromide (0.04 mL, 0.33 mmol) in N,N-dimethylformamide (2 mL) was stirred at 80° C. for 2 h. The reaction mixture was allowed to cool to ambient temperature, and then was partitioned between ethyl acetate (75 mL) and water (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with 40% ethyl acetate in hexanes to afford the title compound as a yellowish solid (0.054 g, 61%): mp 128-130° C.; 1H NMR (300 MHz, CDCl3) δ 7.99 (s, 1H), 7.45 (s, 1H), 7.37-7.25 (m, 7H), 7.12-7.03 (m, 2H), 6.11 (t, J=5.8 Hz, 1H), 5.30 (s, 2H), 4.61 (d, J=5.8 Hz, 2H), 2.54 (s, 3H); MS (ES+) m/z 407.2 (M+1).

Workup

temperatureto cool to ambient temperature
customwas partitioned between ethyl acetate (75 mL) and water (50 mL)
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography
washeluted with 40% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-ba848926a34f4f91a1f45682b50ff602
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258160B2

Reaction notes

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