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)-6-oxo-6H-pyridazin-1-yl]-ethyl}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 564208Notes

Reaction equation

HRID 564208 reaction equation
C(OC1C=CN(CC(C2C=CC(CO)=CC=2)=O)C(=O)C=1)C1C=CC=CC=1.[Br:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:34][O:35][C:36]2[CH:41]=[N:40][NH:39][C:38](=[O:42])[CH:37]=2)=[N:32][CH:33]=1.[C:43]([O:47][C:48]([N:50]1[CH2:59][CH2:58][C:57]2[C:52](=[CH:53][C:54]([CH2:60][CH2:61]OS(C3C=CC(C)=CC=3)(=O)=O)=[CH:55][CH:56]=2)[CH2:51]1)=[O:49])([CH3:46])([CH3:45])[CH3:44]>>[C:43]([O:47][C:48]([N:50]1[CH2:59][CH2:58][C:57]2[C:52](=[CH:53][C:54]([CH2:60][CH2:61][N:39]3[C:38](=[O:42])[CH:37]=[C:36]([O:35][CH2:34][C:31]4[CH:30]=[CH:29][C:28]([Br:27])=[CH:33][N:32]=4)[CH:41]=[N:40]3)=[CH:55][CH:56]=2)[CH2:51]1)=[O:49])([CH3:46])([CH3:45])[CH3:44]

Participants

4

Reactant 3

HCID 580427197-[2-(toluene-4-sulfonyloxy)ethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl esterHCID 580428555-(5-Bromo-pyridin-2-ylmethoxy)-2H-pyridazin-3-oneHCID 670068424-Benzyloxy-1-[2-(4-hydroxymethyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one

Product 1

HCID 670074847-{2-[4-(5-Bromo-pyridin-2-ylmethoxy)-6-oxo-6H-pyridazin-1-yl]-ethyl}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Procedure

7-{2-[4-(5-Bromo-pyridin-2-ylmethoxy)-6-oxo-6H-pyridazin-1-yl]-ethyl}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester is prepared following preparation 15b from 1.13 g (4.00 mmol) 5-(5-bromo-pyridin-2-ylmethoxy)-2H-pyridazin-3-one (preparation 25b) and 1.73 g (4.00 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-81ed419c65f9461cbb2b56249be5dde8
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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