Water → 6-[2-Amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-1,3-benzodioxole-5-carbaldehyde

HRID 1631107Notes

Reaction equation

Br[C:2]1[C:3]([CH:11]=[O:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].O.[NH2:20][C:21]1[N:30]=[C:29]([C:31]([N:33]2[CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34]2)=[O:32])[C:28]2[C:23](=[CH:24][CH:25]=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:27]=2)[N:22]=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]>[NH2:20][C:21]1[N:30]=[C:29]([C:31]([N:33]2[CH2:34][C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:41]2)=[O:32])[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:2]3[C:3]([CH:11]=[O:12])=[CH:4][C:5]4[O:9][CH2:8][O:7][C:6]=4[CH:10]=3)[CH:27]=2)[N:22]=1

Participants

Conditions

Temperature: 120 °C

Procedure

280 mg of 6-bromo-1,3-benzodioxole-5-carbaldehyde, 331 mg of potassium carbonate, 22 μl of water and 49 mg of [1,1′-bis(diphenylphosphino)ferrocene]-palladium(II) dichloride are added to a solution of 500 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 50 ml of ethanol under argon. The mixture is heated at 120° C. for 4 h; 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.

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-586e1854e4b14244ac44f173912e7f4a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791129B2

Reaction notes

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