Ethyl Acetate → 2-(3',4',5'-Trimethoxy-[1,1'-biphenyl]-4-yl)benzo[d]oxazole-5-amine

HRID 63029Notes

Reaction equation

HRID 63029 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH:30]=1)([O-])=O.C(OCC)(=O)C>CO.[Pd]>[CH3:25][O:24][C:22]1[CH:23]=[C:18]([C:15]2[CH:16]=[CH:17][C:12]([C:10]3[O:11][C:7]4[CH:6]=[CH:5][C:4]([NH2:1])=[CH:30][C:8]=4[N:9]=3)=[CH:13][CH:14]=2)[CH:19]=[C:20]([O:28][CH3:29])[C:21]=1[O:26][CH3:27]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 1182226045-Nitro-2-(3',4',5'-trimethoxy-[1,1'-biphenyl]-4-yl)benzo[d]oxazol e

Product 1

HCID 1182226142-(3',4',5'-Trimethoxy-[1,1'-biphenyl]-4-yl)benzo[d]oxazole-5-amineYield 74.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

22 mg (0.0541 mmol) of 5-nitro-2-(3′,4′,5′-trimethoxy-[1,1′-biphenyl]-4-yl)benzo[d]oxazol e was dissolved in methanol, and then, 10% Pd/C was added thereto under hydrogen gas atmosphere. The mixed solution was stirred for 4 hours, and ethyl acetate was added thereto to filter with a celite pad. The filtered solution was concentrated under reduced pressure. Afterwards, the reaction solution was subjected to a silica gel column chromatography (ethyl acetate/normal-hexane at a volume ratio of 1:1) to obtain 15.2 mg (yield=74.6%) of 2-(3′,4′,5′-trimethoxy-[1,1′-biphenyl]-4-yl)benzo[d]oxazole-5-amine (Derivative #7).

Workup

  1. filtrationto filter with a celite pad
  2. concentrationThe filtered solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1bbc92c9cf6b422a882a571478e3113b
Source dataset
uspto-grants-2016_09
Patent number
US09447054B2

Reaction notes

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