Water → Ethyl 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)-quinazolin-6-yl]benzoate

HRID 1037680Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])O1.C(=O)([O-])[O-].[K+].[K+].O.[NH2:28][C:29]1[N:38]=[C:37]([C:39]([N:41]2[CH2:49][C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH2:42]2)=[O:40])[C:36]2[C:31](=[CH:32][CH:33]=[C:34](I)[CH:35]=2)[N:30]=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]>[NH2:28][C:29]1[N:38]=[C:37]([C:39]([N:41]2[CH2:42][C:43]3[C:48](=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:49]2)=[O:40])[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:9]3[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=3[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:35]=2)[N:30]=1

Participants

Conditions

Temperature: 120 °C

Procedure

11.66 g of ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, 10.29 g of potassium carbonate, 0.67 ml of water and 912.4 mg of [1,1′-bis-(diphenylphosphino)ferrocene]palladium(II)dichloride are added to a solution of 15 g of 2-amino-6-iodo-4-(1,3-dihydroisoindol-2-ylcarbonyl)quinazoline in 200 ml of ethanol under argon. The mixture is heated at 120° C. for min, giving a clear solution. The hot solution is filtered through kieselguhr. On cooling, ethyl 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)-quinazolin-6-yl]benzoate crystallises out.

Workup

customgiving a clear solution
filtrationThe hot solution is filtered through kieselguhr
temperatureOn cooling
customethyl 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)-quinazolin-6-yl]benzoate crystallises out

Sources & evidence

ORD record: ord-8f5bf6a587644440b241a810c5a30a1a
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546565B2

Reaction notes

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