Cesium carbonate → Ethyl 1-(6-{2-[(4-iodobenzyl)oxy]phenyl}pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1255167

반응식

HRID 1255167 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.[I:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH4+].[Cl-]>CN(C=O)C>[I:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[N:13]=[C:12]([N:14]3[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]3)[CH:11]=[CH:10][CH:9]=2)=[CH:31][CH:30]=1

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 9542584-Iodobenzyl bromideHCID 136298134Ethyl 1-[6-(2-hydroxylphenyl)pyridine-2-yl]-5-trifluoromethyl-1H-pyrazole-4-carboxylate

생성물 1

HCID 67159424Ethyl 1-(6-{2-[(4-iodobenzyl)oxy]phenyl}pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of the title compound from Example 1 Step B (304 mg, 0.81 mmol) in DMF (2.7 mL) were added 4-iodobenzyl bromide (359 mg, 1.21 mmol) and cesium carbonate (788 mg, 2.42 mmol). After 12 h, the reaction mixture was poured into sat. aq. NH4Cl and extracted with EtOAc. The organic phase was separated, dried over sodium sulfate, filtered, 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 594.4 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.13 (s, 1H), 8.08 (d, J=8.0 Hz, 1H), 7.94 (dd, J=7.5, 1.5 Hz, 1H), 7.88 (t, J=8.0 Hz, 1H), 7.68 (d, J=8.0 Hz, 2H), 7.54 (d, J=8.0 Hz, 1H), 739-7.35 (m, 1H), 7.14-7.12 (m, 1H), 7.11 (d, J=8.0 Hz, 2H), 7.02 (d, J=8.0 Hz, 1H), 5.09 (s, 2H), 4.39 (q, J=7.0 Hz, 2H), 1.39 (t, J=7.0 Hz, 3H).

후처리

  1. extractionextracted with EtOAc
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (0 to 25% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-22aedc9459714a5194cb1a136665b7f9
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455638B2

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