Water → HCID 56943109, compound

HRID 1631150Notes

Reaction equation

Br[C:2]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[CH3:10].C(=O)([O-])[O-].[K+].[K+].O.[NH2:24][C:25]1[N:34]=[C:33]([C:35]([N:37]2[CH2:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:38]2)=[O:36])[C:32]2[C:27](=[CH:28][CH:29]=[C:30](B3OC(C)(C)C(C)(C)O3)[CH:31]=2)[N:26]=1>C(O)C.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]>[NH2:24][C:25]1[N:34]=[C:33]([C:35]([N:37]2[CH2:38][C:39]3[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:45]2)=[O:36])[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:2]3[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:3]=3[CH2:4][N:5]3[CH2:9][CH2:8][CH2:7][CH:6]3[CH3:10])[CH:31]=2)[N:26]=1

Participants

Conditions

Temperature: 120 °C

Procedure

136 mg of 1-(2-bromo-4,5-difluorobenzyl)-2-methylpyrrolidine, 100 mg of potassium carbonate, 7 μl of water and 17 mg of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride are added to a solution of 150 mg of [2-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone in 4 ml of ethanol under argon. The mixture is heated at 120° C. for 30 min; the hot mixture is filtered through kieselguhr, and the filtrate is evaporated and purified by chromatography (reversed phase HPLC).

Workup

filtrationthe hot mixture is filtered through kieselguhr
customthe filtrate is evaporated
custompurified by chromatography (reversed phase HPLC)

Sources & evidence

ORD record: ord-1ecd24550abf489e9b6d6adc85be5227
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791129B2

Reaction notes

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