4-Pyridinecarboxaldehyde → 2-(4-tert-butyl-phenyl)-8-[(pyridin-4-ylmethyl)-amino]-3,4-dihydro-2H-isoquinolin-1-one

HRID 133113Notes

Reaction equation

HRID 133113 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)[CH2:8][CH2:7]2.[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+]>C(Cl)Cl>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([N:9]2[CH2:8][CH2:7][C:6]3[C:11](=[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:10]2=[O:12])=[CH:14][CH:15]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 691593468-amino-2-(4-tert-butyl-phenyl)-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 116396022-(4-tert-butyl-phenyl)-8-[(pyridin-4-ylmethyl)-amino]-3,4-dihydro-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the amine (Step E) and CH2Cl2 (5 mL) was added 4-pyridinecarboxaldehyde and NaBH(OAc)3. The reaction was stirred at RT for 18 h. Purification by silica flash chromatography (25-75% EtOAc:hexane) gave the desired product as a light-yellow oil. MS m/e 386 (M+H)+. Calc'd for C25H27N3O-385.50.

Workup

  1. customPurification by silica flash chromatography (25-75% EtOAc:hexane)

Sources & evidence

ORD record
ord-8048b786ccd048468355b73b0220e0d0
Source dataset
uspto-grants-2008_06
Patent number
US07390820B2

Reaction notes

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