7-[2-(toluene-4-sulfonyloxy)ethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester → 7-{2-[4-(5-Bromo-pyridin-2-ylmethoxy)-2-oxo-2H-pyridin-1-yl]-ethyl}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 564185Notes

Reaction equation

HRID 564185 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][NH:13][C:12](=[O:16])[CH:11]=2)=[N:6][CH:7]=1.[C:17]([O:21][C:22]([N:24]1[CH2:33][CH2:32][C:31]2[C:26](=[CH:27][C:28]([CH2:34][CH2:35]OS(C3C=CC(C)=CC=3)(=O)=O)=[CH:29][CH:30]=2)[CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>>[C:17]([O:21][C:22]([N:24]1[CH2:33][CH2:32][C:31]2[C:26](=[CH:27][C:28]([CH2:34][CH2:35][N:13]3[CH:14]=[CH:15][C:10]([O:9][CH2:8][C:5]4[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=4)=[CH:11][C:12]3=[O:16])=[CH:29][CH:30]=2)[CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 580427197-[2-(toluene-4-sulfonyloxy)ethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl esterHCID 670074364-(5-bromo-pyridin-2-ylmethoxy)-1H-pyridin-2-one

Product 1

HCID 670065517-{2-[4-(5-Bromo-pyridin-2-ylmethoxy)-2-oxo-2H-pyridin-1-yl]-ethyl}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Procedure

7-{2-[4-(5-Bromo-pyridin-2-ylmethoxy)-2-oxo-2H-pyridin-1-yl]-ethyl}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester is prepared following example 24.1 from 562 mg (2.00 mmol) 4-(5-bromo-pyridin-2-ylmethoxy)-1H-pyridin-2-one (preparation 22.2) and 863 mg (2.00 mmol) 7-[2-(toluene-4-sulfonyloxy)-ethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (preparation 7).

Sources & evidence

ORD record
ord-45dd19302ce44bad8c7cf1342fa86124
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

Loading…