Potassium Carbonate → 4'-(4-Bromo-2-propoxy-5-formylimidazol-1-ylmethyl)-3'-fluorobiphenyl-2-carboxylic acid t-butyl ester

HRID 475676ノート

反応式

HRID 475676 の反応式
[Br:1][C:2]1[N:6]=[C:5]([O:7][CH2:8][CH2:9][CH3:10])[NH:4][C:3]=1[CH:11]=[O:12].[C:13]([O:17][C:18]([C:20]1[C:21]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32]Br)=[C:28]([F:34])[CH:27]=2)=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:13]([O:17][C:18]([C:20]1[C:21]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][N:4]3[C:3]([CH:11]=[O:12])=[C:2]([Br:1])[N:6]=[C:5]3[O:7][CH2:8][CH2:9][CH3:10])=[C:28]([F:34])[CH:27]=2)=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 53375348Tert-butyl 4'-bromomethyl-3'-fluoro-biphenyl-2-carboxylateHCID 178458929HCID 178458929、化合物

生成物 1

HCID 598309054'-(4-Bromo-2-propoxy-5-formylimidazol-1-ylmethyl)-3'-fluorobiphenyl-2-carboxylic acid t-butyl ester収率 98.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5-Bromo-2-propoxy-3H-imidazole-4-carbaldehyde (2.1 g, 8.8 mmol), 4′-bromomethyl-3′-fluorobiphenyl-2-carboxylic acid t-butyl ester (3.2 g, 8.8 mmol) and potassium carbonate (3.6 g, 26.4 mmol) were dissolved in DMF (100 mL). The solution was stirred until the reaction was complete, as determined by HPLC. The mixture was extracted with EtOAc (200 mL), washed with saturated aqueous NaCl (4×100 mL), dried over MgSO4, evacuated to dryness, and purified by flash chromatography (EtOAc/hexanes) to yield compound A (4.5 g).

後処理

  1. extractionThe mixture was extracted with EtOAc (200 mL)
  2. washwashed with saturated aqueous NaCl (4×100 mL)
  3. dry with materialdried over MgSO4
  4. customevacuated to dryness
  5. custompurified by flash chromatography (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-a8f5e7d4804c496fa64dc67e55bf7a37
出典データセット
uspto-grants-2014_01
特許番号
US08637562B2

反応ノート

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