Cesium carbonate → HCID 131736446, compound

HRID 1056779Notes

Reaction equation

HRID 1056779 reaction equation
[F:1][C:2]1([F:24])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16](Cl)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2Cl)=[O:11])[CH2:4][CH2:3]1.[C:25]1(B(O)O)[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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>[F:1][C:2]1([F:24])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([C:2]4[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[C:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=2)=[O:11])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 38629021-Cyclohexenylboronic acidHCID 1185559652,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluorocyclohexylmethyl)-amide

Product 1

HCID 131736446HCID 131736446, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was synthesized according to the procedure described in example 125 using 2,6-dichloro-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexyl methyl)-amide, cyclohexene-1-yl-boronic acid, cesium carbonate and tetrakis(triphenylphosphine)palladium (0). 1H NMR (400 MHz, DMSO-d6): δ 8.83 (t, J=5.9 Hz, 1H), 7.89-8.00 (m, 3H), 7.73-7.76 (m, 1H), 6.91 (s, 1H), 3.27 (t, J=6.2 Hz, 2H), 2.65-2.66 (m, 2H), 2.31-2.32 (m, 2H), 1.86-2.01 (m, 2H), 1.74-1.76 (m, 3H), 1.65-1.67 (m, 6H), 1.27-1.30 (m, 2H). m/z: 419 [M+H]+

Sources & evidence

ORD record
ord-ae5c7f84eb8141b9b8a6eef79f62ad9e
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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