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

HRID 475676노트

반응식

HRID 475676 반응식
[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]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 53375348Tert-butyl 4'-bromomethyl-3'-fluoro-biphenyl-2-carboxylateHCID 178458929HCID 178458929, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a8f5e7d4804c496fa64dc67e55bf7a37
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637562B2

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