4-Aminobiphenyl → 4-(Biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid methyl ester

HRID 2266852Notes

Reaction equation

HRID 2266852 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.[CH3:14][O:15][C:16]([C:18]1[O:19][C:20]([CH3:25])=[C:21]([CH:23]=O)[CH:22]=1)=[O:17].C([BH3-])#N.[Na+]>CO>[CH3:14][O:15][C:16]([C:18]1[O:19][C:20]([CH3:25])=[C:21]([CH2:23][NH:7][C:4]2[CH:3]=[CH:2][C:1]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][CH:5]=2)[CH:22]=1)=[O:17]

Participants

5

Reactant 3

HCID 71024-AminobiphenylHCID 5003444Sodium cyanoborohydrideHCID 15503958Methyl 4-formyl-5-methylfuran-2-carboxylate

Product 1

HCID 588241954-(Biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid methyl esterYield 29.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of biphenyl-4-ylamine (150 mg, 0.883 mmoles) and 4-formyl-5-methyl-furan-2-carboxylic acid methyl ester (157) (135 mg, 0.803 mmoles) in methanol (2.0 ml) was stirred over molecular sieves (type 3 Å) for 1 hour. Sodium cyanoborohydride (55 mg, 0.883 mmoles) was added and the mixture stirred for 18 hour at room temperature. The mixture was concentrated and partitioned between ethyl acetate (25 ml) and saturated aqueous sodium bicarbonate (30 ml). The aqueous phase was re-extracted with ethyl acetate (2×25 ml) and the combined extracts were washed with brine (50 ml) and dried (MgSO4). After removal of the solvent, the residue was purified by flash chromatography, using a gradient elution of petrol/diethyl ether 9:1 v/v to 4:1 v/v, to afford compound 158 (75 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate (25 ml) and saturated aqueous sodium bicarbonate (30 ml)
  3. extractionThe aqueous phase was re-extracted with ethyl acetate (2×25 ml)
  4. washthe combined extracts were washed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customAfter removal of the solvent
  7. customthe residue was purified by flash chromatography
  8. washa gradient elution of petrol/diethyl ether 9:1 v/v to 4:1 v/v

Sources & evidence

ORD record
ord-bccbe69bed21458e889eecc4f2657732
Source dataset
uspto-grants-2010_12
Patent number
US07858644B2

Reaction notes

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