Hydrochloric Acid → 2-(4-Tert-butyl-phenyl)-3-methyl-7-[(pyridin-4-ylmethyl)-amino]-2,3-dihydro-isoindol-1-one

HRID 2251865Notes

Reaction equation

HRID 2251865 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=1)[CH:7]2[CH3:22].[N:23]1[CH:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].Cl.C([O-])(O)=O.[Na+]>ClCCCl.CCOC(C)=O>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([N:8]2[CH:7]([CH3:22])[C:6]3[C:10](=[C:2]([NH:1][CH2:29][C:26]4[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=4)[CH:3]=[CH:4][CH:5]=3)[C:9]2=[O:11])=[CH:17][CH:16]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 133894-PyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 690303807-Amino-2-(4-tert-butyl-phenyl)-3-methyl-2,3-dihydro-isoindol-1-one

Product 1

HCID 112000032-(4-Tert-butyl-phenyl)-3-methyl-7-[(pyridin-4-ylmethyl)-amino]-2,3-dihydro-isoindol-1-one

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 7-amino-2-(4-tert-butyl-phenyl)-3-methyl-2,3-dihydro-isoindol-1-one (0.11 g, 0.37 mmol, Step G), 4-pyridinecarboxaldehyde (0.14 mL, 0.93 mmol), and NaBH(OAc)3 (0.41 g, 1.85 mmol) in 5 mL of 1,2-dichloroethane was stirred at RT for 48 h, and diluted with 20 mL of EtOAc. 1.0 N HCl (aq) was added to bring pH to 1-2. After stirring for 30 min, NaHCO3 (aq) was added to bring pH to 10. The organic portion was washed with brine, condensed, and the titled compound was obtained as a white solid after flash column chromatography (0 to 35% of EtOAc in CH2Cl2). MS (ES+): 386.3 (M+H)+. Calc'd for C25H27N3O-385.50

Workup

  1. stirringAfter stirring for 30 min
  2. washThe organic portion was washed with brine, condensed

Sources & evidence

ORD record
ord-04fb64098b904be39b824cc218e6bda4
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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