Sodium borohydride → HCID 59436025, compound

HRID 1802474Notes

Reaction equation

HRID 1802474 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH:11][C:12]2[C:21]3[CH:20]=[CH:19][NH:18][C:17](=[O:22])[C:16]=3[C:15]3[CH:23]=[C:24]([Br:27])[CH:25]=[CH:26][C:14]=3[N:13]=2)=[C:6]([Cl:28])[CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[Br:27][C:24]1[CH:25]=[CH:26][C:14]2[N:13]=[C:12]([NH:11][C:7]3[C:6]([Cl:28])=[CH:5][C:4]([CH:1]([OH:3])[CH3:2])=[CH:9][C:8]=3[Cl:10])[C:21]3[CH:20]=[CH:19][NH:18][C:17](=[O:22])[C:16]=3[C:15]=2[CH:23]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59436026HCID 59436026, compound

Product 1

HCID 59436025HCID 59436025, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-[(4-acetyl-2,6-dichlorophenyl)amino]-9-bromobenzo[c]-2,6-naphthyridin-1(2H)-one (700 mg, 1.47 mmol) in methanol (10 mL) was added sodium borohydride (444 mg, 11.7 mmol) at 0° C. and the reaction mixture was stirred for 30 min. The solution was extracted with EtOAc and water, dried over MgSO4, filtered, and concentrated to afford the crude material. Purification by column chromatography on silica gel (100% CH2Cl2 to 70% CH2Cl2/30% MeOH) afforded the title compound.

Workup

  1. extractionThe solution was extracted with EtOAc and water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford the crude material
  6. customPurification by column chromatography on silica gel (100% CH2Cl2 to 70% CH2Cl2/30% MeOH)

Sources & evidence

ORD record
ord-3ae8216660384f37b2cebb41cc9a7c87
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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