Dichloromethane → HCID 18446586, compound

HRID 1268876Notes

Reaction equation

[C:1]([C:3]1[C:4]2[S:12][C:11](Br)=[CH:10][C:5]=2[C:6](=[O:9])[NH:7][CH:8]=1)#[N:2].[C:14]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].ClCCl>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([C:3]1[C:4]2[S:12][C:11]([C:21]3[CH:22]=[CH:23][C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:19][CH:20]=3)=[CH:10][C:5]=2[C:6](=[O:9])[NH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 7-cyano-2-bromo-4-oxo-4,5-dihydrothieno[3,2-c]-pyridine (2.0 g, 7.84 mmol) in DMF (40 mL) and water (15 mL) was added 4-t-butylphenyl boronic acid (2.1 g, 11.8 mmol), potassium carbonate (1.4 g, 10.1 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (0.192 g, 0.23 mmol). The resulting mixture was stirred under nitrogen for 4 h at 80° C. After this time the mixture was diluted with DMF (20 mL), filtered through celite to remove palladium residues and water (100 mL) added. The precipitated solid was filtered, washed thoroughly with water and dried in air by suction at room temperature providing 1.4 g of 100 which was used without further analysis or purification.

Workup

filtrationfiltered through celite
customto remove palladium residues and water (100 mL)
additionadded
filtrationThe precipitated solid was filtered
washwashed thoroughly with water
customdried in air by suction at room temperature

Sources & evidence

ORD record: ord-c01373661ab847a4b9aab8b218d3c940
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199119B2

Reaction notes

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