Dimethylformamide → HCID 59283904, 화합물

HRID 1810137노트

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HRID 1810137 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)=[CH:28][C:27]=2[F:34])=[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>O>[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])=[CH:28][C:27]=2[F:34])=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 59283905HCID 59283905, 화합물HCID 178458929HCID 178458929, 화합물

생성물 1

HCID 59283904HCID 59283904, 화합물수율 59.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

5-Bromo-2-propoxy-3H-imidazole-4-carbaldehyde (3.7 g, 15.7 mmol), 4′-bromomethyl-2′-fluorobiphenyl-2-carboxylic acid t-butyl ester (5.7 g, 15.7 mmol) and potassium carbonate (6.5 g, 47.0 mmol) were dissolved in DMF (50 mL, 646 mmol), and stirred at room temperature until the reaction was complete, as determined by HPLC. Water (100 mL) was added and the mixture was extracted with EtOAc (2×), washed with saturated aqueous NaCl (2×), dried over MgSO4, filtered and concentrated to yield a yellow oil. The oil was purified by flash chromatography (2-20% EtOAc/hexanes) to yield compound A (4.8 g) as a colorless oil.

후처리

  1. extractionthe mixture was extracted with EtOAc (2×)
  2. washwashed with saturated aqueous NaCl (2×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a yellow oil
  7. customThe oil was purified by flash chromatography (2-20% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-94cd51d8302141a0b7e0935e7d1d6236
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362061B2

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