Water → HCID 24954698, compound

HRID 1879140Notes

Reaction equation

[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[C:18](Cl)[N:17]=2)=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:30]1(/[CH:36]=[CH:37]/B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>COC>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[C:18](/[CH:37]=[CH:36]/[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:17]=2)=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(6-chloro-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide (40 mg, 0.12 mmol, 1.0 equiv) in dimethyl ether (0.6 mL) was added Na2CO3 (25 mg, 0.23 mmol, 2.0 equiv), trans-2-phenylvinyl boronic acid (43 mg, 0.29 mmol, 2.5 equiv), CombiPhos Pd-6 (6.0 mg, 0.01 mmol, 0.1 equiv) and water (0.2 mL) in a sealed tube. The reaction was heated in the microwave oven at 100° C. for 25 min. After cooling, the solvent was removed in vacuo. The crude product was purified by column chromatography [SiO2, methanol/dichloromethane, 0:100 to 5:95, v/v] to give 4-methyl-2-[6-((E)-styryl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide (32 mg, 67%). 1H NMR (400 MHz, CD2Cl2) δ 9.17 (s, 1H), 8.64 (s, 1H), 7.83 (d, J=16.0 Hz, 1H), 7.62-7.64 (m, 2H), 7.28-7.43 (m, 8H), 7.19 (d, J=16.0 Hz, 1H), 6.25 (bs, 1H), 4.61 (d, J=1.0 Hz, 2H), 2.74 (s, 3H); HRMS (M+H)+=413.14.

Workup

temperatureAfter cooling
customthe solvent was removed in vacuo
customThe crude product was purified by column chromatography [SiO2, methanol/dichloromethane, 0:100 to 5:95, v/v]

Sources & evidence

ORD record: ord-5f90a1f8ed58410897ee6f588624ed7b
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314138B2

Reaction notes

Loading…