Cesium carbonate → HCID 118566705, compound

HRID 1056784Notes

Reaction equation

HRID 1056784 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][C@@H:4]([CH3:8])[CH2:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:31]1(B2OC(C)(C)C(C)(C)O2)[CH2:35][CH2:34][CH2:33][CH:32]=1>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>[OH:1][C@:2]1([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([C:31]4[CH2:35][CH2:34][CH2:33][CH:32]=4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])[CH2:7][CH2:6][CH2:5][C@@H:4]([CH3:8])[CH2:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 154866112-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 1185666992,6-dichloro-quinoline-5-carboxylic acid ((1R,3R)-1-hydroxy-3-methyl-cyclohexylmethyl)-amide

Product 1

HCID 118566705HCID 118566705, 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 ((1R,3R)-1-hydroxy-3-methyl-cyclohexylmethyl)-amide, cesium carbonate, 2-cyclopent-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane and tetrakis(triphenylphosphine)Palladium (0). 1H NMR (400 MHz, DMSO-d6): δ 8.63 (t, J=5.91 Hz, 1H), 8.06 (d, J=8.92 Hz, 1H), 7.96 (dd, J=4.43, 8.92 Hz, 2H), 7.73 (d, J=9.01 Hz, 1H), 6.89 (s, 1H), 4.18 (s, 1H), 3.29 (s, 1H), 2.85-2.87 (m, 2H), 2.48-2.49 (m, 2H), 1.96-2.03 (m, 1H), 1.45-1.78 (m, 6H), 1.28-1.32 (m, 5H). m/z: 399.2 [M+H]+

Sources & evidence

ORD record
ord-5fc4d308ae8b4bd48813f112c523a5d7
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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