Cesium carbonate → 6-Chloro-2-(3-oxo-cyclopent-1-enyl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexyl methyl)-amide

HRID 1056795Notes

Reaction equation

HRID 1056795 reaction equation
[F:1][C:2]1([F:25])[CH2:7][CH2:6][C:5]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17](Cl)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])([OH:8])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C(C)(C)OB([C:40]2[CH2:44][CH2:43][C:42](=[O:45])[CH:41]=2)O1>>[F:1][C:2]1([F:25])[CH2:7][CH2:6][C:5]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([C:40]4[CH2:44][CH2:43][C:42](=[O:45])[CH:41]=4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])([OH:8])[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 668228763-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclopenten-1-oneHCID 1185560922,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexylmethyl)-amide

Product 1

HCID 1185667066-Chloro-2-(3-oxo-cyclopent-1-enyl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexyl methyl)-amide

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-1-hydroxy-cyclo hexyl methyl)-amide, cesium carbonate, 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-cyclopent-2-enone and tetrakis(triphenyl phosphine)palladium(0). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.83-8.86 (bs, 1H), 8.27-8.29 (m, 1H), 8.22 (d, J=8.8 Hz, 1H), 8.12-8.14 (m, 1H), 7.87 (d, J=9.1 Hz, 1H), 7.12 (s, 1H), 4.72 (s, 1H), 3.42-3.44 (m, 2H), 3.20-3.22 (m, 2H), 2.55-2.57 (m, 2H), 2.07-2.10 (m, 2H), 1.89-2.01 (m, 2H), 1.70-1.77 (m, 4H).

Sources & evidence

ORD record
ord-cb3e447e4d634e7f893f4a8e5cee2aa4
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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