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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 2406209
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HRID 2406209 반응식
[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
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참가 물질

7

반응물 3

HCID 11776TriphenylphosphineHCID 75617Benzyl acrylateHCID 1358703069-Bromo-2-(4-methylphenyl)-2,6-dihydro[1,2,4]triazolo[4,3-c]quinazoline-3,5-dione

생성물 1

HCID 136340046Benzyl (2E)-3-[2-(4-methylphenyl)-3,5-dioxo-2,6-dihydro[1,2,4]triazolo[4,3-c]quinazolin-9-yl]acrylate수율 47%

시약·촉매·용매 3

HCID 167845
palladium(II) acetate
촉매
HCID 6228Dimethylformamide용매
HCID 8471Triethylamine용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-343bfd0b6f6448788d88d9f08406c88a
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08809355B2

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