Potassium Iodide → 2,2-Dimethyl-propionic acid 7-(2-chloro-3,6-difluoro-phenyl)-5-(2,2-difluoro-ethyl)-6-oxo-5,6-dihydro-pyrido[2,3-b]pyrazin-8-yl ester

HRID 1512064Notes

Reaction equation

Br[CH2:2][CH:3]([F:5])[F:4].[Cl:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[C:8]=1[C:15]1[C:24](=[O:25])[NH:23][C:18]2=[N:19][CH:20]=[CH:21][N:22]=[C:17]2[C:16]=1[O:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[Cl:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[C:8]=1[C:15]1[C:24](=[O:25])[N:23]([CH2:2][CH:3]([F:5])[F:4])[C:18]2=[N:19][CH:20]=[CH:21][N:22]=[C:17]2[C:16]=1[O:26][C:27](=[O:32])[C:28]([CH3:30])([CH3:29])[CH3:31]

Participants

Conditions

Temperature: 120 °C

Procedure

1-Bromo-2,2-difluoroethane (0.113 g) was added to a mixture of 2,2-dimethyl-propionic acid 7-(2-chloro-3,6-difluoro-phenyl)-6-oxo-5,6-dihydro-pyrido[2,3-b]pyrazin-8-yl ester (Example 1.3) (0.126 g), potassium carbonate (0.044 g) and potassium iodide (0.053 g) in acetonitrile (5 ml). The reaction mixture was heated in a microwave for 25 minutes at 120° C. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate, 8:2 to 1:1) to give Compound No. A2 of Table A as a yellow solid (0.083 g).

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate, 8:2 to 1:1)
customto give Compound No

Sources & evidence

ORD record: ord-777390685ae44a898aba8c418c1d2323
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217055B2

Reaction notes

Loading…