1-(4'-Hydroxymethyl-4,6-dinitro-biphenyl-3-yl)-propan-2-one → [4-(2-methyl-6-nitro-1H-indol-5-yl)-phenyl]-methanol

HRID 1773537Notes

Reaction equation

HRID 1773537 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([N+:18]([O-])=O)=[C:11]([CH2:21][C:22](=O)[CH3:23])[CH:10]=2)=[CH:5][CH:4]=1>[Pd].C(OCC)(=O)C>[CH3:23][C:22]1[NH:18][C:12]2[C:11]([CH:21]=1)=[CH:10][C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1)=[C:14]([N+:15]([O-:17])=[O:16])[CH:13]=2.[OH:16][NH:15][C:14]1[CH:13]=[C:12]2[C:11]([CH:21]=[C:22]([CH3:23])[NH:18]2)=[CH:10][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1

Participants

5

Reactant 1

HCID 580561251-(4'-Hydroxymethyl-4,6-dinitro-biphenyl-3-yl)-propan-2-one

Product 2

HCID 66665074[4-(2-methyl-6-nitro-1H-indol-5-yl)-phenyl]-methanolHCID 86661370(4-(6-(Hydroxyamino)-2-methyl-1h-indol-5-yl)phenyl)methanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(4′-hydroxymethyl-4,6-dinitro-biphenyl-3-yl)-propan-2-one (200 mg) and palladium on carbon (10%, 80 mg) in ethyl acetate was shaken in a Parr apparatus under hydrogen atmosphere (50 PSI) overnight. The reaction mixture was then filtered on a CELITE™ pad, the filtrate was evaporated under reduced pressure and the crude residue was purified by flash chromatography to afford [4-(2-methyl-6-nitro-1H-indol-5-yl)-phenyl]-methanol and [4-(6-hydroxyamino-2-methyl-1H-indol-5-yl)-phenyl]-methanol. The two products were combined and dissolved in dichloromethane (5 mL). Zinc dust (a large excess) and glacial acetic acid (1 mL) were added and the resulting mixture was heated at 70° C. for 30 minutes. The reaction mixture was then filtered on a CELITE™ pad, the filter cake was washed with ethyl acetate. The filtrate was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (MeOH/DCM, 5/95) to give 55 mg of [4-(6-amino-2-methyl-1H-indol-5-yl)-phenyl]-methanol. MS=253 [M+H]+.

Workup

  1. filtrationThe reaction mixture was then filtered on a CELITE™ pad
  2. customthe filtrate was evaporated under reduced pressure
  3. customthe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-dae74c01603048b2b7b3818ba5595619
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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