Triphenylphosphine → tert-Butyl 2-(7-(3-Cyano-5-(trifluoromethoxy)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

HRID 515659

반응식

HRID 515659 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1.O[CH2:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([O:32][C:33]([F:36])([F:35])[F:34])[CH:31]=1)[C:27]#[N:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:27]([C:26]1[CH:25]=[C:24]([CH:31]=[C:30]([O:32][C:33]([F:34])([F:36])[F:35])[CH:29]=1)[CH2:23][O:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1)#[N:28]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 668475343-(Hydroxymethyl)-5-(trifluoromethoxy)benzonitrileHCID 67249455tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

생성물 1

HCID 67250450tert-Butyl 2-(7-(3-Cyano-5-(trifluoromethoxy)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate수율 22.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To an ice-cooled solution of tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (131 mg, 0.456 mmol), 3-(hydroxymethyl)-5-(trifluoromethoxy)benzonitrile (114 mg, 0.524 mmol) and triphenylphosphine (179 mg, 0.684 mmol) in THF (3 mL) was added diisopropyl diazene-1,2-dicarboxylate (0.135 mL, 0.684 mmol) dropwise. After stirring at 0° C. for 15 min, the cooling bath was removed and the mixture was stirred at 23° C. for 3 h and then concentrated. The residue was purified by preparative TLC to provide the title compound as a yellow solid (50 mg). LCMS m/z=487.4 [M+H]+.

후처리

  1. customthe cooling bath was removed
  2. stirringthe mixture was stirred at 23° C. for 3 h
  3. concentrationconcentrated
  4. customThe residue was purified by preparative TLC

출처 및 근거

ORD 기록
ord-ecde021396eb457595907aaac6ea0b3e
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108969B2

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