Triphenylphosphine → HCID 67159279, 화합물

HRID 1255191

반응식

HRID 1255191 반응식
[OH:1][C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([N:15]2[C:19]([C:20]([F:23])([F:22])[F:21])=[C:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:17]=[N:16]2)[CH:12]=[CH:11][CH:10]=1.[CH3:29][C:30]1[CH:37]=[C:36]([CH3:38])[CH:35]=[CH:34][C:31]=1[CH2:32]O.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>C(Cl)Cl>[CH3:29][C:30]1[CH:37]=[C:36]([CH3:38])[CH:35]=[CH:34][C:31]=1[CH2:32][O:1][C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([N:15]2[C:19]([C:20]([F:23])([F:22])[F:21])=[C:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:17]=[N:16]2)[CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 278092,4-Dimethylbenzyl alcoholHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 136356801Ethyl 1-[6-(2-hydroxy-3-iodophenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

생성물 1

HCID 67159279HCID 67159279, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of the title compound from Example 15 Step A (200 mg, 0.397 mmol), 2,4-dimethylbenzyl alcohol (81.0 mg, 0.596 mmol), and triphenylphosphine (156 mg, 0.596 mmol) in DCM (2 mL) was added diisopropyl azodicarboxylate (0.114 mL, 0.596 mmol), and the resulting mixture was stirred at ambient temperature. After 18 h, the reaction mixture was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 20% EtOAc in hexanes, then 20 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 594.8 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.17 (s, 1H), 8.02 (d, J=8.0 Hz, 1H), 7.92 (d, J=7.5 Hz, 1H), 7.85-7.81 (m, 2H), 7.60 (d, J=7.5 Hz, 1H), 7.13 (d, J=7.5 Hz, 1H), 7.05 (t, J=7.5 Hz, 1H), 6.95-6.92 (m, 2H), 4.69 (s, 2H), 4.41 (q, J=7.0 Hz, 2H), 2.30 (s, 3H), 2.17 (s, 3H), 1.43 (t, J=7.0 Hz, 3H).

후처리

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customPurification by flash chromatography on silica gel (0 to 20% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-54b228aa5b28431eb7c0d5793fb2a938
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455638B2

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