Dimethylformamide → HCID 59283904, compound

HRID 1517751Notes

Reaction equation

HRID 1517751 reaction equation
[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]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 59283905HCID 59283905, compoundHCID 178458929HCID 178458929, compound

Product 1

HCID 59283904HCID 59283904, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-814a98dd1c1f4cf9af104a5c6731d1bb
Source dataset
uspto-grants-2012_07
Patent number
US08232306B2

Reaction notes

Loading…