Sodium hydride → [1-(4-Methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-acetic acid methyl ester

HRID 720434ノート

反応式

HRID 720434 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:18])[NH:15][CH2:16][CH2:17][C:12]=3[C:11]([C:19]([F:22])([F:21])[F:20])=[N:10]2)=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:26][C:27]([O:29][CH3:30])=[O:28]>CN(C)C=O>[CH3:30][O:29][C:27](=[O:28])[CH2:26][N:15]1[CH2:16][CH2:17][C:12]2[C:11]([C:19]([F:22])([F:20])[F:21])=[N:10][N:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[C:13]=2[C:14]1=[O:18]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 218914731-(4-Methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one

生成物 1

HCID 10339907[1-(4-Methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-acetic acid methyl ester収率 74%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Part D: 1-(4-Methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one (1.0 g, 3.213 mmol) was dissolved in N,N-dimethylformamide (20 mL) and cooled to 0° C. Sodium hydride (60%, 0.321 g, 8.032 mmol) was added followed by methyl bromoacetate (0.608 mL, 6.425 mmol). The reaction was stirred at rt overnight. The reaction was quenched with 1N hydrochloric acid (100 mL), extracted with ethyl acetate (3×100 mL), washed with water (2×100 mL), washed with brine (1×100 mL), dried over MgSO4, concentrated, and purified by flash chromatography using 0–100% ethyl acetate/hexanes gradient as the eluent to afford the title compound (0.91 g, 74%): 1H NMR (CDCl3) δ 7.45 (d, j=8.8 Hz, 2H), 6.96 (d, j=9.2 Hz, 2H), 4.25 (s, 2H), 3.84 (s, 3H), 3.78 (t, j=7.0 Hz, 2H), 3.75 (m, 3H), 3.02 (t, j=6.8 Hz, 2H) ppm.

後処理

  1. customThe reaction was quenched with 1N hydrochloric acid (100 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washwashed with water (2×100 mL)
  4. washwashed with brine (1×100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-6da1089b6e84453e810c0f66a18c1173
出典データセット
uspto-grants-2006_11
特許番号
US07135469B2

反応ノート

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