Potassium Carbonate → HCID 59830900, compound

HRID 1802909Notes

Reaction equation

HRID 1802909 reaction equation
[CH2:1]([C:5]1[NH:9][C:8]([CH:10]=[O:11])=[C:7]([Cl:12])[N:6]=1)[CH2:2][CH2:3][CH3:4].[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][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:9]3[C:8]([CH:10]=[O:11])=[C:7]([Cl:12])[N:6]=[C:5]3[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:28][CH:27]=2)=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 178418251HCID 178418251, compound

Product 1

HCID 59830900HCID 59830900, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Butyl-5-chloro-3H-imidazole-4-carbaldehyde (9.9 g, 53.3 mmol), 4′-bromomethylbiphenyl-2-carboxylic acid t-butyl ester (18.5 g, 53.3 mmol), and K2CO3 (7.4 g, 53.3 mmol) were combined in DMF (200 mL) and stirred at room temperature overnight. The reaction was quenched with water, extracted with EtOAc, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The crude mixture was purified by flash chromatography (0-40% EtOAc:hexanes) to yield 21.5 g of intermediate (4a).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. washwashed with saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude mixture was purified by flash chromatography (0-40% EtOAc:hexanes)

Sources & evidence

ORD record
ord-f7da63f770c840008d6a7434d7935e56
Source dataset
uspto-grants-2013_01
Patent number
US08349875B2

Reaction notes

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