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

HRID 2089586Notes

Reaction equation

HRID 2089586 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-766d60b5a5ef4657995ad2d24db6edac
Source dataset
uspto-grants-2013_05
Patent number
US08436038B2

Reaction notes

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