Dimethylformamide → Ethyl 1-[6-(2-{[4-(2-phenylethyl)benzyl]oxy}phenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1255160

반응식

HRID 1255160 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.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.CCO[C:42]([CH3:44])=O>>[C:3]1([CH2:8][CH2:9][C:42]2[CH:44]=[CH:16][C:17]([CH2:23][O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:8]3[N:13]=[C:12]([N:14]4[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]4)[CH:11]=[CH:10][CH:9]=3)=[CH:18][CH:19]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 136298134Ethyl 1-[6-(2-hydroxylphenyl)pyridine-2-yl]-5-trifluoromethyl-1H-pyrazole-4-carboxylate

생성물 1

HCID 67159203Ethyl 1-[6-(2-{[4-(2-phenylethyl)benzyl]oxy}phenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

실험 절차

A vial was charged with the title compound from Example 1 Step B (36.0 mg, 0.095 mmol), cesium carbonate (62.2 mg, 0.191 mmol), and 4-chloromethyl dibenzyl (33.0 mg, 0.143 mmol). DMF (0.5 mL) was added, and the resulting suspension was stirred vigorously. After 2 h, the reaction mixture was diluted with EtOAc and washed with brine. The organic phase was separated and 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 572.5 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.16 (d, J=8.0 Hz, 1H), 8.12 (s, 1H), 7.98 (dd, J=7.5, 1.5 Hz, 1H), 7.86 (t, J=7.5 Hz, 1H), 7.53 (d, J=7.0 Hz, 1H), 7.39-7.36 (m, 1H), 7.29-7.26 (m, 4H), 7.22-7.17 (m, 5H), 7.11 (t, J=7.5 Hz, 1H), 7.07 (d, J=8.5 Hz, 1H), 5.13 (s, 2H), 4.39 (q, J=7.0 Hz, 2H), 2.93 (app s, 4H), 1.39 (t, J=7.0 Hz, 3H).

후처리

  1. washwashed with brine
  2. customThe organic phase was separated
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography on silica gel (0 to 25% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-957345b283874a84bc3891df5dde9ec3
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455638B2

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