Water → 1-Amino-3-(difluoromethyl)-N-phenyl-1H-pyrrole-2-carboxamide

HRID 525022

反応式

HRID 525022 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:11][CH:12]([F:27])[C:13]1[CH:17]=[CH:16][NH:15][C:14]=1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19].C1(P(C2C=CC=CC=2)(=O)[NH2:35])C=CC=CC=1.O>CN(C=O)C>[NH2:35][N:15]1[CH:16]=[CH:17][C:13]([CH:12]([F:11])[F:27])=[C:14]1[C:18]([NH:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:19]

参加物

6

反応物 4

HCID 962WaterHCID 853560DiphenylphosphinamideHCID 2733832Lithium HexamethyldisilazideHCID 709794883-(difluoromethyl)-N-phenyl-1H-pyrrole-2-carboxamide

生成物 1

HCID 709795551-Amino-3-(difluoromethyl)-N-phenyl-1H-pyrrole-2-carboxamide収率 38%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

1.1 ml (1.1 mmol) of a 1M solution of lithium bis(trimethylsilyl)amide was added to a solution of 3-(difluoromethyl)-N-phenyl-1H-pyrrole-2-carboxamide (100 mg, 0.42 mmol) and DPPONH2 (P,P-diphenylphosphinic amide, available from Sigma Aldrich®, cat. no. 5994-87-6) (250 mg, 1,1 mmol) in DMF (4 mL) at room temperature. A thick suspension formed and additional 4 mL of DMF were added. The mixture was stirred at room temperature for 1 hour and then it was poured into 50 mL of water and extracted with ethyl acetate. The aqueous layer was further extracted with ethyl acetate (2×). The combined organic layer was washed with water and brine and was dried over sodium sulphate, filtered and concentrated. The crude product was purified by flash chromatography (0% to 33% AcOEt/Hexanes) to yield 40 mg (38% yield) of the title compound.

後処理

  1. customat room temperature
  2. customA thick suspension formed
  3. extractionextracted with ethyl acetate
  4. extractionThe aqueous layer was further extracted with ethyl acetate (2×)
  5. washThe combined organic layer was washed with water and brine
  6. dry with materialwas dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography (0% to 33% AcOEt/Hexanes)

出典と根拠

ORDレコード
ord-41ba3a249a234264a3f78ed7a26965f2
出典データセット
uspto-grants-2016_05
特許番号
US09340547B2

関連ノート

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