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Cesium carbonate → HCID 58007509、化合物

HRID 1094383
ノート
印刷プレビュー

反応式

HRID 1094383 の反応式
[CH3:1][N:2]1[C:6]([NH:7][C:8](=[O:17])[C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:4]([CH3:18])=[N:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CC(OC)(C)C>[CH3:1][N:2]1[C:6]([N:7]([CH2:30][CH2:31][C:32]2[CH:33]=[CH:34][C:35]([C:38]([F:39])([F:40])[F:41])=[CH:36][CH:37]=2)[C:8](=[O:17])[C:9](=[O:16])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][C:4]([CH3:18])=[N:3]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 149499411-(2-Bromoethyl)-4-(trifluoromethyl)benzene2 回HCID 58007534HCID 58007534、化合物

生成物 1

HCID 58007509HCID 58007509、化合物収率 33.2%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 15413tert-Butyl methyl ether溶媒

実験手順

To a solution of N-(2,5-dimethyl-2H-pyrazol-3-yl)-2-oxo-2-phenyl-acetamide (200 mg, 0.82 mmol) in DMF (2 mL) was added at 0° C. potassium bis(trimethylsilyl)amide (0.91 M in THF, 1.1 mL, 0.99 mmol) over a period of 5 min. The ice bath was removed and the solution was stirred for 1 h at ambient temperature. After the addition of 1-(2-bromo-ethyl)-4-trifluoromethyl-benzene (which might be prepared according to WO2005123748, 250 mg, 0.99 mmol) the reaction mixture was stirred for 18 h at ambient temperature. After the addition of cesium carbonate (1.40 g, 4.11 mmol) and further 1-(2-bromo-ethyl)-4-trifluoromethyl-benzene (996 mg, 3.95 mmol) it was stirred for 20 h at ambient temperature. The resulting mixture was diluted with TBME (15 mL) and washed twice with water (10 mL) and brine (10 mL). The combined aqueous layers were extracted with TBME (15 mL) and the combined organic layers were dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40) afforded the title compound (113 mg, 33%) as a light brown oil. MS m/e: 416.3 [M+H]+.

後処理

  1. customThe ice bath was removed
  2. stirringwas stirred for 18 h at ambient temperature
  3. stirringwas stirred for 20 h at ambient temperature
  4. washwashed twice with water (10 mL) and brine (10 mL)
  5. extractionThe combined aqueous layers were extracted with TBME (15 mL)
  6. dry with materialthe combined organic layers were dried over sodium sulfate
  7. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40)

出典と根拠

ORDレコード
ord-c8f476fd74ca4195af549c10a2335ded
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08133909B2

反応ノート

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