Sodium Hydroxide → HCID 68535385, compound

HRID 2389358Notes

Reaction equation

HRID 2389358 reaction equation
[C:1]1([CH:7]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:33])[N:12]([CH2:14]/[CH:15]=[CH:16]/[C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[CH:20][N:21]4C(OC(C)(C)C)=O)[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO.CCOC(C)=O>[C:1]1([CH:7]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:33])[N:12]([CH2:14]/[CH:15]=[CH:16]/[C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[CH:20][NH:21]4)[CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68535582HCID 68535582, compound

Product 1

HCID 68535385HCID 68535385, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-{(1E)-3-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]-1-propen-1-yl}-1H-indole-1-carboxylate (247 mg) in MeOH (5 mL) was added 1M NaOH aqueous solution (1.5 mL) at ambient temperature. The reaction mixture was stirred for 17 hours at ambient temperature. The resulting mixture was diluted with EtOAc (15 mL) and washed successively with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20-50:50) to give 5-(diphenylmethyl)-1-[(2E)-3-(1H-indol-4-yl)-2-propen-1-yl]-2(1H)-pyridinone.

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20-50:50)

Sources & evidence

ORD record
ord-e7313cf76d264d2bb9e00bf5c9332ce6
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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