Sodium Iodide → N-[1-(2-Hydroxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl]-1,1'-biphenyl-4-carboxamide

HRID 494217Notes

Reaction equation

HRID 494217 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-].[Na+].Br[CH2:35][CH2:36][OH:37]>O1CCOCC1.CCOC(C)=O>[OH: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

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 44415452N-(1,2,3,4-Tetrahydroquinolin-7-yl)-1,1'-biphenyl-4-carboxamide

Product 1

HCID 57682704N-[1-(2-Hydroxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl]-1,1'-biphenyl-4-carboxamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(1,2,3,4-Tetrahydroquinolin-7-yl)-1,1′-biphenyl-4-carboxamide (Example 24) (100 mg, 0.304 mmol), potassium carbonate (126 mg, 0.913 mmol), sodium iodide (9 mg, 0.06 mmol) and 2-bromoethanol (216 ul, 3.04 mmol) in dioxane (1 ml) were heated at 60° C. for 8 d. After cooling to ambient temperature the reaction mixture was diluted with EtOAc (10 ml), filtered and concentrated in vacuo to give the crude product which was purified on a silica SPE column. Elution with an EtOAc/60-80° C. petroleum ether gradient gave the title compound as a beige solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.93 (d, 2H), 7.78 (s, 1H), 7.70 (d, 2H), 7.63 (d, 2H), 7.48 (t, 2H), 7.40 (t, 1H), 7.19 (d, 1H), 6.93 (d, 1H), 6.74 (dd, 1H), 3.87 (m, 2H), 3.49 (t, 2H), 3.35 (m, 2H), 2.75 (t, 2H), 1.97 (m, 3H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customto give the crude product which
  4. customwas purified on a silica SPE column
  5. washElution with an EtOAc/60-80° C. petroleum ether gradient

Sources & evidence

ORD record
ord-481da700570a47798ac6aba799aa3c49
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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