Cesium carbonate → HCID 118566562, compound

HRID 1056781Notes

Reaction equation

HRID 1056781 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]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C(C)(C)OB([C:39]2[CH2:40][CH2:41][O:42][CH2:43][CH:44]=2)O1>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:39]4[CH2:44][CH2:43][O:42][CH2:41][CH:40]=4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 1185559652,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluorocyclohexylmethyl)-amide

Product 1

HCID 118566562HCID 118566562, 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-cyclohexylmethyl)-amide, cesium carbonate, 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran and tetrakis(triphenylphosphine)palladium (0). 1H NMR (400 MHz, DMSO-d6): δ ppm 8.85 (t, J=6.00 Hz, 1H), 7.95-8.05 (m, 3H), 7.77 (d, J=9.00 Hz, 1H), 6.98 (s, 1H), 4.33-4.35 (m, 2H), 3.86 (t, J=5.48 Hz, 2H), 3.26-3.28 (m, 2H), 2.66-2.70 (m, 2H), 2.00-2.07 (m, 2H), 1.74-1.87 (m, 5H), 1.23-1.31 (m, 2H). m/z: 421 [M+H]+

Sources & evidence

ORD record
ord-ff654a6f773c43e0a1ddac565e648ad1
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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