Water → 2-[2-Amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-5-hydroxybenzaldehyde

HRID 1631106Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].O.[NH2:18][C:19]1[N:28]=[C:27]([C:29]([N:31]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32]2)=[O:30])[C:26]2[C:21](=[CH:22][CH:23]=[C:24](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[N:20]=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]>[NH2:18][C:19]1[N:28]=[C:27]([C:29]([N:31]2[CH2:32][C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:39]2)=[O:30])[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:2]3[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=3[CH:4]=[O:5])[CH:25]=2)[N:20]=1

Participants

Conditions

Temperature: 120 °C

Procedure

72 mg of 2-bromo-5-hydroxybenzaldehyde, 100 mg of potassium carbonate, 1 ml of water and 15 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 3 ml of ethanol under argon. The mixture is heated at 120° C. for min; the hot mixture is filtered through kieselguhr, and the filtrate is evaporated. The residue obtained was triturated with 2 ml of acetonitrile, and the precipitate formed was filtered off with suction. Yield: 56 mg (38%) of 2-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-5-hydroxybenzaldehyde; HPLC retention time: 1.67 min.

Workup

filtrationthe hot mixture is filtered through kieselguhr
customthe filtrate is evaporated
customThe residue obtained
customwas triturated with 2 ml of acetonitrile
customthe precipitate formed
filtrationwas filtered off with suction

Sources & evidence

ORD record: ord-6fafe939b0e0482d9358ac54d3df9a6c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791129B2

Reaction notes

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