Dimethylformamide → Methyl 2-(4-tert-butylthiazol-2-yl)benzofuran-5-carboxylate

HRID 1604648Notes

Reaction equation

[C]=O.FC(F)(F)S(O[C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([C:17]3[S:18][CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[N:21]=3)=[CH:14][C:13]=2[CH:26]=1)(=O)=O.C1(OP(CCCP([O:57][C:58]2C=CC=CC=2)(OC2C=CC=CC=2)=O)(OC2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.CN(C)[CH:73]=[O:74]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO>[C:22]([C:20]1[N:21]=[C:17]([C:15]2[O:16][C:12]3[CH:11]=[CH:10][C:9]([C:73]([O:57][CH3:58])=[O:74])=[CH:26][C:13]=3[CH:14]=2)[S:18][CH:19]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 70 °C

Procedure

Carbon monoxide was introduced by bubbling to a mixture of 2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl trifluoromethanesulfonate (6.0 g), palladium acetate (99.7 mg), 1,3-bis(diphenylphosphono)propane (183 mg, 0.44 mmol) and triethylamine (4.13 ml) in a mixed solvent of methanol (15 ml) and N,N-dimethylformamide (30 ml) at room temperature for 1 hour. The mixture was warmed to 70° C. and stirred under carbon monoxide balloon for 3 hours. The resulting mixture was filtered through celite and the residue was washed with ethyl acetate. The filtrate and washing solution was combined and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate-n-hexane as eluent to give methyl 2-(4-tert-butylthiazol-2-yl)benzofuran-5-carboxylate (3.92 g) as a colorless powder.

Workup

filtrationThe resulting mixture was filtered through celite
washthe residue was washed with ethyl acetate
washThe filtrate and washing solution
customevaporated under reduced pressure
customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-438352edabd341d88dfbc1795d420f22
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05994378

Reaction notes

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