Cesium fluoride → HCID 118555944, compound

HRID 1056800Notes

Reaction equation

HRID 1056800 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.[F-].[Cs+].[C:27]([O:31][C:32]([N:34]1[CH2:39][CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:27]([O:31][C:32]([N:34]1[CH2:35][CH:36]=[C:37]([C:16]2[CH:15]=[CH:14][C:13]3[C:18](=[CH:19][CH:20]=[C:21]([Cl:22])[C:12]=3[C:10](=[O:11])[NH:9][CH2:8][CH:5]3[CH2:6][CH2:7][C:2]([F:24])([F:1])[CH2:3][CH2:4]3)[N:17]=2)[CH2:38][CH2:39]1)=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 1185559652,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluorocyclohexylmethyl)-amide

Product 1

HCID 118555944HCID 118555944, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, 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 fluoride, 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester and bis(triphenylphosphine)palladium(II) dichloride. 1H NMR (400 MHz, DMSO-d6): δ 8.85 (t, J=5.82 Hz, 1H), 8.03-8.05 (m, 1H), 7.94-8.00 (m, 2H), 7.78 (d, J=9.01 Hz, 1H), 6.89 (s, 1H), 4.12 (s, 2H), 3.57 (t, J=5.5 Hz, 2H), 3.28 (t, J=6.23 Hz, 2H), 2.73 (s, 2H), 2.02-2.04 (m, 2H), 1.74-1.87 (m, 5H), 1.43 (s, 9H), 1.30-1.32 (m, 2H). m/z: 519.0 [M+H]+

Sources & evidence

ORD record
ord-571281f143034b5f87add0dbcea9e7f0
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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