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Triphenylphosphine → Ethyl 1-[6-(2-{[4-(1,4-dioxaspiro[4.5]dec-8-yl)benzyl]oxy}phenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1255180
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HRID 1255180 반응식
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([N:14]2[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]2)[CH:11]=[CH:10][CH:9]=1.[O:28]1[C:32]2([CH2:37][CH2:36][CH:35]([C:38]3[CH:43]=[CH:42][C:41]([CH2:44]O)=[CH:40][CH:39]=3)[CH2:34][CH2:33]2)[O:31][CH2:30][CH2:29]1.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>[O:28]1[C:32]2([CH2:33][CH2:34][CH:35]([C:38]3[CH:43]=[CH:42][C:41]([CH2:44][O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=4[C:8]4[N:13]=[C:12]([N:14]5[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]5)[CH:11]=[CH:10][CH:9]=4)=[CH:40][CH:39]=3)[CH2:36][CH2:37]2)[O:31][CH2:30][CH2:29]1
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참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 29921578[4-(1,4-Dioxaspiro[4.5]dec-8-yl)phenyl]methanolHCID 136298134Ethyl 1-[6-(2-hydroxylphenyl)pyridine-2-yl]-5-trifluoromethyl-1H-pyrazole-4-carboxylate

생성물 1

HCID 67159196Ethyl 1-[6-(2-{[4-(1,4-dioxaspiro[4.5]dec-8-yl)benzyl]oxy}phenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of the title compound from Example 1 Step B (251 mg, 0.67 mmol), the title compound from Example 10 Step C (248 mg, 1.00 mmol), and triphenylphosphine (349 mg, 1.33 mmol) in DCM (3 mL) was added diisopropyl azodicarboxylate (0.259 mL, 1.33 mmol). The resulting mixture was stirred at ambient temperature. After 5 h, the reaction mixture was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 25% EtOAc in hexanes then 25 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 608.06 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.15 (d, J=8.0 Hz, 1H), 8.12 (s, 1H), 7.97 (d, J=8.0 Hz, 1H), 7.85 (t, J=8.0 Hz, 1H), 7.52 (d, J=7.5 Hz, 1H), 7.38-7.35 (m, 1H), 7.29 (d, J=7.5 Hz, 2H), 7.23 (d, J=7.5 Hz, 2H), 7.12-7.06 (m, 2H), 5.12 (s, 2H), 4.38 (q, J=7.0 Hz, 2H), 3.98 (s, 4H), 2.60-2.54 (m, 1H), 1.87-1.65 (m, 8H), 1.39 (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 25% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-efc05277b9384578a278a2a600c5d2ba
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08455638B2

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