Sodium borohydride → HCID 67455110, compound

HRID 639645Notes

Reaction equation

HRID 639645 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:12]=[C:11]([CH2:26][CH:27]=[O:28])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>ClCCl>[CH2:1]([NH:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:12]=[C:11]([CH2:26][CH2:27][OH:28])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86614477HCID 86614477, compound

Product 1

HCID 67455110HCID 67455110, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4,6-Bis-benzylamino-5-nitro-pyridin-2-yl)-acetaldehyde (250 mg, 0.66 mmol) was stirred in 15 ml dichloromethane. Sodium borohydride (38 mg, 0.99 mmol) was added and the solution stirred at ambient temperature overnight. The reaction mixture was partitioned between DCM and water, the organics dried over magnesium sulphate and concentrated to give a crude solid which was purified by column chromatography on silica, eluting with pentane:EtOAc, 4:1 to 1:1 to afford the title compound as a yellow solid, (134 mg, 53%).

Workup

  1. customThe reaction mixture was partitioned between DCM and water
  2. dry with materialthe organics dried over magnesium sulphate
  3. concentrationconcentrated
  4. customto give a crude solid which
  5. customwas purified by column chromatography on silica
  6. washeluting with pentane

Sources & evidence

ORD record
ord-0fae3f8999304de1913402ca10c53260
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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