Triphenylphosphine → Benzyl (2E)-3-[2-(4-methylphenyl)-3,5-dioxo-2,6-dihydro[1,2,4]triazolo[4,3-c]quinazolin-9-yl]acrylate

HRID 2406209Notes

Reaction equation

[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:4])[CH:2]=[CH2:3].Br[C:14]1[CH:23]=[CH:22][C:21]2[NH:20][C:19](=[O:24])[N:18]3[C:25](=[O:35])[N:26]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)[N:27]=[C:17]3[C:16]=2[CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.CCN(CC)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:34][C:31]1[CH:32]=[CH:33][C:28]([N:26]2[C:25](=[O:35])[N:18]3[C:19](=[O:24])[NH:20][C:21]4[CH:22]=[CH:23][C:14](/[CH:3]=[CH:2]/[C:1]([O:5][CH2:6][C:7]5[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=5)=[O:4])=[CH:15][C:16]=4[C:17]3=[N:27]2)=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirred solution of benzyl acrylate (44 μg, 0.274 mmol) and 8a (50.6 mg, 0.137 mmol) in a mixture of 8 mL of DMF and 4 mL of NEt3, was added Pd(OAc)2 (3.06 mg, 13.7 mmol) and triphenylphosphine (7.14 mg, 27.4 μmol) in a seal tube. The tube was sealed under argon and the mixture was stirred at 120° C. for 15 h. The mixture was cooled and concentrated to dryness in vacuo and the crude product was precipitated from acetone to give 17 as a white solid (29 mg, 47%). mp: 242° C.

Workup

customThe tube was sealed under argon
temperatureThe mixture was cooled
concentrationconcentrated to dryness in vacuo
customthe crude product was precipitated from acetone

Sources & evidence

ORD record: ord-343bfd0b6f6448788d88d9f08406c88a
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809355B2

Reaction notes

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