Methyl 3-bromopropanoate → N-[1-(2-Methoxycarbonylethyl)-1,2,3,4-tetrahydroquinolin-7-yl]-1,1'-biphenyl-4-carboxamide

HRID 494216Notes

Reaction equation

HRID 494216 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.Br[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30]>>[CH3:32][O:31][C:29]([CH2:28][CH2:27][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)=[O:30]

Participants

3

Reactant 2

HCID 76934Methyl 3-bromopropanoateHCID 44415452N-(1,2,3,4-Tetrahydroquinolin-7-yl)-1,1'-biphenyl-4-carboxamide

Product 1

HCID 57682694N-[1-(2-Methoxycarbonylethyl)-1,2,3,4-tetrahydroquinolin-7-yl]-1,1'-biphenyl-4-carboxamide

Procedure

Using the procedure outlined in Example 29, the title compound was prepared from N-(1,2,3,4-tetrahydroquinolin-7-yl)-1,1′-biphenyl-4-carboxamide (Example 24) (66 mg, 0.2 mmol) and methyl 3-bromopropionate (264 ul, 2.4 mmol) as a yellow gum. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.94 (d, 2H), 7.76 (br, 1H), 7.70 (d, 2H), 7.63 (d, 2H), 7.48 (t, 2H), 7.40 (t, 1H), 7.04 (d, 1H), 6.93 (d, 1H), 6.79 (dd, 1H), 3.69 (s, 3H), 3.65 (t, 2H), 3.31 (m, 2H), 2.72 (t, 2H), 2.67 (t, 2H), 1.93 (m, 2H).

Sources & evidence

ORD record
ord-5d52db5481ca4dc18ba86a9e9e5af621
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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