Potassium Iodide → N-[1-(2-n-Propyloxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl]-1,1'-biphenyl-4-carboxamide

HRID 494218Notes

Reaction equation

HRID 494218 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:16][CH:15]=3)=[O:13])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:35][CH2:36][O:37][CH2:38][CH2:39][CH3:40]>CN(C=O)C>[CH2:38]([O:37][CH2:36][CH2:35][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)=[O:13])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1)[CH2:39][CH3:40]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1235061-(2-Chloroethoxy)propaneHCID 44415452N-(1,2,3,4-Tetrahydroquinolin-7-yl)-1,1'-biphenyl-4-carboxamide

Product 1

HCID 57682697N-[1-(2-n-Propyloxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl]-1,1'-biphenyl-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(1,2,3,4-Tetrahydroquinolin-7-yl)-1,1′-biphenyl-4-carboxamide (Example 24) (66 mg, 0.2 mmol), potassium carbonate (41 mg, 0.3 mmol), potassium iodide (100 mg, 0.6 mmol) and 2-chloroethyl-n-propyl ether (38 ul, 0.3 mmol) in DMF (1 ml) were heated at 60° C. for 17 h then 100° C. for 48 h. After cooling to ambient temperature the reaction mixture was purified on a silica SPE column. Elution with 8% EtOAc/60-80° C. petroleum ether gave the title compound as a yellow solid. 1H NMR (250 MHz, CDCl3) δ (ppm): 7.93 (d, 2H), 7.72 (br, 1H), 7.70 (d, 2H), 7.63 (d, 2H), 7.48 (t, 2H), 7.40 (t, 1H), 7.03 (d, 1H), 6.92 (d, 1H), 6.74 (dd, 1H), 3.66 (t, 2H), 3.50 (t, 2H), 3.40 (m, 4H), 2.73 (t, 2H), 1.93 (qn, 2H), 1.58 (sx, 2H), 0.91 (t, 3H).

Workup

  1. customwas purified on a silica SPE column
  2. washElution with 8% EtOAc/60-80° C. petroleum ether

Sources & evidence

ORD record
ord-6b3d25b7d7c041919662a2344299de9d
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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