Water → HCID 59190101, compound

HRID 1645277Notes

Reaction equation

HRID 1645277 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[O:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([N:26]3[CH2:32][CH2:31][CH2:30][N:29]([CH3:33])[CH2:28][CH2:27]3)=[O:25])[CH:19]=2)=[CH:16][CH:17]=1.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH:5]2[CH2:12][C:13]1[O:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([N:26]3[CH2:32][CH2:31][CH2:30][N:29]([CH3:33])[CH2:28][CH2:27]3)=[O:25])[CH:19]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 66774402HCID 66774402, compound

Product 1

HCID 59190101HCID 59190101, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5-chloro-3-((5-(3-(4-methyl-1,4-diazepane-1-carbonyl)phenyl)furan-2-yl)methylene)indolin-2-one (24 mg) in methanol (4 ml) was added sodium borohydride (8 mg). The reaction was stirred at room temperature for 5 min. Water was added and the product was extracted with dichloromethane, dried with sodium sulfate and concentrated under vacuum to give 5-chloro-3-((5-(3-(4-methyl-1,4-diazepane-1-carbonyl)phenyl)furan-2-yl)methyl)indolin-2-one as orange powder. LCMS (ES): >95% pure, m/z 464 [M+1]+.

Workup

  1. extractionthe product was extracted with dichloromethane
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-40f0ae790dac4e49823adabcc82fa2ce
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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