Cesium carbonate → 6-Chloro-2-(3-oxo-cyclopent-1-enyl)-quinoline-5-carboxylic acid (1-hydroxy-3-methylcyclo hexyl methyl)-amide

HRID 1056792Notes

Reaction equation

HRID 1056792 reaction equation
[OH:1][C:2]1([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])[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[CH2:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C(C)(C)OB([C:39]2[CH2:43][CH2:42][C:41](=[O:44])[CH:40]=2)O1>C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[OH:1][C:2]1([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([C:39]4[CH2:43][CH2:42][C:41](=[O:44])[CH:40]=4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[CH2:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 668228763-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclopenten-1-oneHCID 866233652,6-Dichloro-quinoline-5-carboxylic acid (1-hydroxy-3methyl-cyclohexylmethyl)-amide

Product 1

HCID 1185667076-Chloro-2-(3-oxo-cyclopent-1-enyl)-quinoline-5-carboxylic acid (1-hydroxy-3-methylcyclo hexyl methyl)-amide

Reagents, catalysts & solvents 1

HCID 178477754HCID 178477754, compoundCatalyst

Procedure

The title compound was synthesized according to the procedure described in example 125 using 2,6-dichloro-quinoline-5-carboxylic acid (1-hydroxy-3-methyl-cyclohexylmethyl)-amide, cesium carbonate, 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-cyclopent-2-enone and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II). 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.70 (t, J=6.04 Hz, 1H), 8.28-8.22 (m, 2H), 8.12 (d, J=9.21 Hz, 1H), 7.86 (d, J=9.03 Hz, 1H), 7.13 (t, J=1.64 Hz, 1H), 4.21 (s, 1H), 3.22-3.20 (m, 2H), 2.56-2.54 (m, 2H), 1.73 (t, J=3.41 Hz, 1H), 1.62-1.56 (m, 4H), 1.48-1.45 (m, 1H), 1.32-1.25 (m, 1H), 1.06-1.00 (m, 1H), 0.84 (d, J=6.63 Hz, 3H), 0.77-0.74 (m, 1H). m/z: 413.2 [M+H]+

Sources & evidence

ORD record
ord-91cccf9e4fa646a0ac16af659511bcce
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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