Sodium Bicarbonate → HCID 12015828, compound

HRID 2301817Notes

Reaction equation

HRID 2301817 reaction equation
[C:1]([C:5]1[CH:31]=[CH:30][C:8]([C:9]([NH:11][C:12]2[C:13]([NH:18][C:19]([C:21]3[CH:29]=[C:28]4[C:24]([CH:25]=[CH:26][NH:27]4)=[CH:23][CH:22]=3)=[O:20])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>C(O)(=O)C.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][C:12]2[C:13]([NH:18][C:19]([C:21]3[CH:29]=[C:28]4[C:24]([CH2:25][CH2:26][NH:27]4)=[CH:23][CH:22]=3)=[O:20])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:30][CH:31]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 12015826HCID 12015826, compound

Product 1

HCID 12015828HCID 12015828, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirring solution of N2-(4-t-butylbenzoyl)-N1-(6-indolylcarbonyl)-1,2-benzenediamine (0.1 g, 0.24 mmol) in acetic acid (1 mL) was added NaBH3CN (0.046 g, 0.73 mmol). After 2 h, the mixture was diluted with water (10 mL), the pH was basified with conc aq NaHCO3 and the aqueous phase was extracted twice with ethyl acetate. The combined ethyl acetate phase was washed with water and brine, then dried with MgSO4, filtered and concentrated in vacuo to give 70 mg (70%) of white solid.

Workup

  1. extractionthe aqueous phase was extracted twice with ethyl acetate
  2. washThe combined ethyl acetate phase was washed with water and brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4cf75701efc41649df022d025538d1b
Source dataset
uspto-grants-2002_12
Patent number
US06500851B2

Reaction notes

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