Methane → HCID 53875955, compound

HRID 487188Notes

Reaction equation

HRID 487188 reaction equation
Br[C:2]1[CH:22]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[C:5]2[N:6]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:7]([CH2:9][CH2:10][CH2:11][CH3:12])=[N:8][C:4]=2[CH:3]=1.[C:27]1(C)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1(B(O)O)C=CC=CC=1.C>CO.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[NH4+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH2:9]([C:7]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[C:5]2[C:21]([C:23]([O:25][CH3:26])=[O:24])=[CH:22][C:2]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:3][C:4]=2[N:8]=1)[CH2:10][CH2:11][CH3:12]

Participants

10

Reactant 4

HCID 297MethaneHCID 1140TolueneHCID 66827Phenylboronic AcidHCID 19094223HCID 19094223, compound

Product 1

HCID 53875955HCID 53875955, compoundYield 68%

Reagents, catalysts & solvents 5

HCID 14923Ammonium HydroxideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 10340Sodium CarbonateSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 5-bromo-2-n-butyl-1-(2-chlorophenyl)methyl-1H-benzimidazole-7-carboxylate (600 mg, 1.38 mmol), tetrakis(triphenylphosphine)palladium(O) (50 mg), toluene (3 mL) and 2M sodium carbonate solution (1.5 mL) was treated with a solution of phenylboronic acid (200 mg, 1.64 mmol) in methanol (0.3 mL). The resulting mixture was vigorously stirred under an argon atmosphere and heated at 80° C. for 18 hours. The cooled reaction was diluted with methylene chloride, 2M sodium carbonate solution and a few drops of ammonium hydroxide solution. Some insolubles were filtered, the organic phase was separated, dried (magnesium sulfate) and concentrated to 0.55 g of crude product. TLC on silica with 4:1 hexane/ethyl acetate gave an Rf of 0.33 for the product; the starting material had an Rf of 0.43. The crude product was dissolved in methylene chloride, treated with activated charcoal and the filtrate was concentrated to a small volume and chilled. The separated off-white crystals were filtered to afford 0.41 g (68%) of methyl 2-n-butyl-1-(2-chlorophenyl)methyl-5-phenyl-1H-benzimidazole-7-carboxylate; mp 103°-105° C.

Workup

  1. customThe cooled reaction
  2. filtrationSome insolubles were filtered
  3. customthe organic phase was separated
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated to 0.55 g of crude product
  6. customTLC on silica with 4:1 hexane/ethyl acetate gave an Rf of 0.33 for the product
  7. concentrationthe filtrate was concentrated to a small volume
  8. temperaturechilled
  9. filtrationThe separated off-white crystals were filtered

Sources & evidence

ORD record
ord-7f673e94ce8d4afeb9cb7a2c6c8cb480
Source dataset
uspto-grants-1994_03
Patent number
US05294631

Reaction notes

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