Dimethylformamide → HCID 59351636, compound

HRID 1889413Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:8]2[CH:39]=[C:38]([CH2:40][CH3:41])[S:37][C:9]=2[N:10]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]#[N:36])=[CH:25][CH:24]=2)[C:11](=[O:21])[C:12]=1[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CCCC)CCCC)CCC.CN(C)C=O>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)=O>[CH2:40]([C:38]1[S:37][C:9]2[N:10]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:29]4[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:27][CH:28]=3)[C:11](=[O:21])[C:12]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:7][C:8]=2[CH:39]=1)[CH3:41]

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 7-[(2′-cyanobiphenyl-4-yl)methyl]-2-ethyl-6-oxo-5-(2-phenylethyl)-6,7-dihydrothieno[2,3-b]pyridin-4-yl trifluoromethanesulfonate (1 g), palladium acetate (0.018 g), triphenylphosphine (0.042 g), tributylamine (1.18 mL) and N,N-dimethylformamide (20 mL) was added formic acid (0.12 mL), and the mixture was stirred under argon atmosphere at 70° C. for 1 hr. The reaction mixture was diluted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as colorless crystals (0.34 g, 45%).

Workup

washwashed successively with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-8d447a62ad81435489f467d142c488bb
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501750B2

Reaction notes

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