Triethylsilane → HCID 118559735, compound

HRID 1056806Notes

Reaction equation

HRID 1056806 reaction equation
[F:1][C:2]1([F:32])[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:23]4[CH2:24][CH2:25][N:26]([CH:29]([CH3:31])[CH3:30])[CH2:27][CH:28]=4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1.C([SiH](CC)CC)C>[Pd]>[F:32][C:2]1([F:1])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([CH:23]4[CH2:24][CH2:25][N:26]([CH:29]([CH3:30])[CH3:31])[CH2:27][CH2:28]4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 118566709HCID 118566709, compound

Product 1

HCID 118559735HCID 118559735, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title compound was synthesized according to the procedure described in example 126 using 6-chloro-2-(1-isopropyl-1,2,3,6-tetrahydro-pyridin-4-yl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexylmethyl)-amide, palladium on carbon and triethylsilane. 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.79 (t, J=5.92 Hz, 1H), 8.01 (d, J=8.71 Hz, 1H), 7.97 (dd, J=0.5, 9.02 Hz, 1H), 7.76 (d, J=9.02 Hz, 1H), 7.60 (d, J=8.81 Hz, 1H), 3.27 (t, J=6.23 Hz, 2H), 2.91 (d, J=7.61 Hz, 3H), 2.82 (s, 1H), 2.25 (s, 2H), 2.03 (d, J=9.4 Hz, 2H), 1.86-1.74 (m, 9H), 1.30-1.24 (m, 2H), 1.00 (d, J=5.8 Hz, 6H). m/z: 464.20 [M+H]+

Sources & evidence

ORD record
ord-6a75c81d62444c75971c16426678cf1a
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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