Sodium borohydride → HCID 19010476, compound

HRID 1741669Notes

Reaction equation

HRID 1741669 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N+:23]([O-])=O)[CH:21]=2)[N:16]([CH2:26][C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][C:31]([Cl:37])=[CH:32][CH:33]=3)[N:28]=2)[CH:15]=1)[C:6]([O:8][CH3:9])=[O:7].[BH4-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([NH2:23])[CH:21]=2)[N:16]([CH2:26][C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][C:31]([Cl:37])=[CH:32][CH:33]=3)[N:28]=2)[CH:15]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19010472HCID 19010472, compound

Product 1

HCID 19010476HCID 19010476, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the nitroindole from Step 1 (185 mg, 0.36 mmol) in THF (3 ml) containing NaBH4 /S (200 mg) was heated at reflux for 1 hr. The solvent was removed and the residue was partitioned between EtOAc and H2O. The organic layer was dried, evaporated, and concentrated to give the crude amine (185 mg) which was used directly in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hr
  3. customThe solvent was removed
  4. customthe residue was partitioned between EtOAc and H2O
  5. customThe organic layer was dried
  6. customevaporated
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1722332c1a374461925bcc16d835c35e
Source dataset
uspto-grants-1994_08
Patent number
US05334597

Reaction notes

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