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

HRID 1512065Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

2-Fluoroethyl bromide 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) (0.20 g), potassium carbonate (0.207 g) and potassium iodide (catalytic amount) in N,N-dimethylformamide (10 ml). The reaction mixture was heated in the microwave for 20 minutes at 120° C. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 1:1) to give Compound No. C9 of Table C as a yellow solid (0.103 g).

Workup

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

Sources & evidence

ORD record: ord-3263ca96aa804827b06332c3211a75d7
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217055B2

Reaction notes

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