Ethyl Acrylate → HCID 131723982, compound

HRID 1180196Notes

Reaction equation

HRID 1180196 reaction equation
Br[C:2]1[CH:33]=[CH:32][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:4][CH:3]=1.[C:34]([O:38][CH2:39][CH3:40])(=[O:37])[CH:35]=[CH2:36]>>[F:31][C:28]1[CH:29]=[CH:30][C:25]([N:8]2[CH2:9][CH2:10][C:11]3[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:12]=3)[CH:7]2[CH2:6][C:5]2[CH:32]=[CH:33][C:2](/[CH:36]=[CH:35]/[C:34]([O:38][CH2:39][CH3:40])=[O:37])=[CH:3][CH:4]=2)=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 8821Ethyl AcrylateHCID 18186409HCID 18186409, compound

Product 1

HCID 131723982HCID 131723982, compoundYield 90.4%

Procedure

The title compound was prepared as described in Example 135, using 1-(4-bromobenzyl)-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline (1.22 g, 2.43 mmol) and ethyl acrylate (0.50 g, 5.0 mmol) to provide the title compound (1.146 g, 90% yield): 1H NMR (CDCl3) 7.65 (d, 1H), 7.33-7.44 (m, 7H), 7.02 (d, 2H), 6.92 (m, 2H), 6.69-6.78 (m, 5H), 6.39 (d, 1H), 5.03 (s, 2H), 4.76 (t, 1H), 4.26 (q, 2H), 3.55 (m, 1H), 3.48 (m 1H), 3.18 (dd, 1H), 2.95 (m, 2H), 2.67 (dt, 1H), 1.31 (t, 3H); ES-MS m/z 522 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-caba846234864f819fde5adbe6c4cd16
Source dataset
uspto-grants-2007_10
Patent number
US07279489B2

Reaction notes

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