Water → HCID 56943216, compound

HRID 1631146Notes

Reaction equation

Br[C:2]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:3]=1[CH2:4][NH:5][C:6]([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+].O.[NH2:23][C:24]1[N:33]=[C:32]([C:34]([N:36]2[CH2:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:37]2)=[O:35])[C:31]2[C:26](=[CH:27][CH:28]=[C:29](B3OC(C)(C)C(C)(C)O3)[CH:30]=2)[N:25]=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]>[NH2:23][C:24]1[N:33]=[C:32]([C:34]([N:36]2[CH2:37][C:38]3[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:44]2)=[O:35])[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:2]3[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:3]=3[CH2:4][NH:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH:30]=2)[N:25]=1

Participants

Conditions

Temperature: 120 °C

Procedure

184 mg of (2-bromo-4,5-difluorobenzyl)-tert-butylamine, 166 mg of potassium carbonate, 11 μl of water and 25 mg of [1,1′-bis(diphenylphosphino)ferrocene]-palladium(II) dichloride are added to a solution of 250 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 10 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
customand purified by chromatography (reversed phase HPLC)

Sources & evidence

ORD record: ord-063a21399b7c426a978823c6029bb6f8
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791129B2

Reaction notes

Loading…