Sodium Carbonate → HCID 59198451, compound

HRID 1896530Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)=[N:10][CH:11]=[C:12]([C:15]#[N:16])[C:13]=3[S:14][C:4]=2[CH:3]=1.[F:27][C:28]([F:39])([F:38])[C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][NH:17][C:9]2[C:8]3[C:5]4[CH:6]=[CH:7][C:2]([C:32]5[CH:33]=[CH:34][C:29]([C:28]([F:39])([F:38])[F:27])=[CH:30][CH:31]=5)=[CH:3][C:4]=4[S:14][C:13]=3[C:12]([C:15]#[N:16])=[CH:11][N:10]=2)=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture containing 7-bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile (Example 12, Step 9), 4-trifluoromethylphenylboronic acid (1.7 equiv), Pd(OAc)2 (0.14 equiv), Ph3P (0.42 equiv), Na2CO3 2 M (2.9 equiv) in 1-PrOH/DMF (3/1) (0.09 M) was degassed and heated at 100° C. for 3 h. The resulting mixture was concentrated to dryness, and the crude solid was washed successively with H2O and MeOH to provide the title compound as a brown solid.

Workup

customwas degassed
concentrationThe resulting mixture was concentrated to dryness
washthe crude solid was washed successively with H2O and MeOH

Sources & evidence

ORD record: ord-8249977c92bd404f8b4b2224fdffd542
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518964B2

Reaction notes

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