Ethanol → 2-(4-Chlorophenyl)-6H,7H-thieno[2,3-c]pyridin-7-one

HRID 2384876Notes

Reaction equation

Br[C:2]1[S:11][C:5]2[C:6](=[O:10])[NH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.COCCOC>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[S:11][C:5]3[C:6](=[O:10])[NH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Combine 2-bromo-6H-thieno[2,3-c]pyridin-7-one (25.0 g, 108.7 mmol), 4-chlorophenylboronic acid (18.7 g, 119.5 mmol), sodium carbonate (23.5 g, 217.3 mmol), ethanol (121 mL), 1,2-dimethoxyethane (604 mL), and water (121 mL). Purge the mixture with nitrogen for 20 min. Add tetrakis(triphenylphosphine)palladium (3.77 g, 3.26 mmol). Heat the reaction mixture at 85° C. overnight. Allow the reaction to cool to RT. Reduce the reaction solvent volume to half on a rotory evaporator. Filter the mixture with water (2×400 mL), ether (400 mL), and ethylacetate (20 mL) and dry the solids in vacuo at 40° C. to give 25.4 g (89%) of the title compound. LC-MS/ES m/z (35Cl) 262.0 [M+H]+.

Workup

customPurge the mixture with nitrogen for 20 min
customthe reaction
temperatureto cool to RT
customon a rotory evaporator
filtrationFilter the mixture with water (2×400 mL), ether (400 mL), and ethylacetate (20 mL)
customdry the solids in vacuo at 40° C.

Sources & evidence

ORD record: ord-cd1b044e04da41eba1d9a16cf3848dab
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263772B2

Reaction notes

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