Water → 5-Hydroxymethyl-2-phenyl-7-nitro-1H-indole

HRID 1466499Notes

Reaction equation

HRID 1466499 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[NH:11][C:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:9]2)=O)C.[Li+].[BH4-].O>CO>[OH:3][CH2:4][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[NH:11][C:10]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[CH:9]2

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 68474038ethyl 7-nitro-2-phenyl-1H-indole-5-carboxylate

Product 1

HCID 684763775-Hydroxymethyl-2-phenyl-7-nitro-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Phenyl-7-nitro-1H-indole-5-carboxylic acid ethyl ester (10 g, 29 mmol) prepared in Step A of Example 28 was dissolved in methanol (100 mL), and LiBH4 (1M THF solution, 4 mL) was added thereto at 0° C. After warming to room temperature, the mixture was stirred for 3 h. A small amount of water was added to quench the reaction. Methanol was removed under reduced pressure. 1N HCl was added to the residue, which was then extracted with EtOAc, dried, and used in the next reaction without further purification.

Workup

  1. customat 0° C
  2. customto quench
  3. customthe reaction
  4. customMethanol was removed under reduced pressure
  5. addition1N HCl was added to the residue, which
  6. extractionwas then extracted with EtOAc
  7. customdried
  8. customused in the next reaction without further purification

Sources & evidence

ORD record
ord-8c40c6821ca041f380897dae2a427065
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

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