Potassium Phosphate, Tribasic → 4-{(E)-2-[5-(3,4-Difluorophenyl)pyridin-2-yl]vinyl}-7,7-dimethyl-5-oxo-4,5,6,7,8,9-hexahydro-1H-pyrazolo[3,4-b]quinoline 3-cyclopropylmethylcarboxamide

HRID 1630420Notes

Reaction equation

HRID 1630420 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[CH:10]2[C:19]3[C:18](=[O:20])[CH2:17][C:16]([CH3:22])([CH3:21])[CH2:15][C:14]=3[NH:13][C:12]3[NH:23][N:24]=[CH:25][C:11]2=3)=[N:6][CH:7]=1.[CH2:26]1[CH:28]([CH2:29][C:30]([NH2:32])=[O:31])[CH2:27]1.[F:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][C:39]=1[F:40].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:33][C:34]1[CH:35]=[C:36]([C:2]2[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[CH:10]3[C:19]4[C:18](=[O:20])[CH2:17][C:16]([CH3:22])([CH3:21])[CH2:15][C:14]=4[NH:13][C:12]4[NH:23][N:24]=[CH:25][C:11]3=4)=[N:6][CH:7]=2)[CH:37]=[CH:38][C:39]=1[F:40].[CH2:27]1[CH:28]([CH2:29][C:30]([NH2:32])=[O:31])[CH2:26]1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343373,4-Difluorobenzeneboronic acidHCID 1371958004-[(E)-2-(5-Bromopyridin-2-yl)vinyl]-7,7-dimethyl-5-oxo-4,5,6,7,8,9-hexahydro-1H-pyrazolo[3,4-b]quinoline 3-cyclopropylmethylcarboxamide

Product 1

HCID 1371958024-{(E)-2-[5-(3,4-Difluorophenyl)pyridin-2-yl]vinyl}-7,7-dimethyl-5-oxo-4,5,6,7,8,9-hexahydro-1H-pyrazolo[3,4-b]quinoline 3-cyclopropylmethylcarboxamide

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

The title compound is prepared according to procedure C from 125 mg of 4-[(E)-2-(5-bromopyridin-2-yl)vinyl]-7,7-dimethyl-5-oxo-4,5,6,7,8,9-hexahydro-1H-pyrazolo[3,4-b]quinoline-3-cyclopropylmethylcarboxamide, 60 mg of 3,4-difluorophenylboronic acid, 134 mg of K3PO4 and 37 mg of 1,1′-bis(diphenylphosphino)ferrocenepalladium dichloride.

Sources & evidence

ORD record
ord-273e0180e1094852985fd8f418249347
Source dataset
uspto-grants-2014_07
Patent number
US08791133B2

Reaction notes

Loading…