Ethyl 2-(5-nitropyridin-2-YL)acetate → [5-Amino-6-(4,4-dimethyl-cyclohex-1-enyl)-pyridin-2-yl]-acetic acid ethyl ester

HRID 1190175Notes

Reaction equation

HRID 1190175 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][N:7]=1)[CH3:2].[CH3:16][C:17]1([CH3:26])[CH2:22][CH2:21][C:20](B(O)O)=[CH:19][CH2:18]1>>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([C:20]2[CH2:21][CH2:22][C:17]([CH3:26])([CH3:16])[CH2:18][CH:19]=2)[N:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 18670679Ethyl 2-(5-nitropyridin-2-YL)acetateHCID 441195554,4-Dimethylcyclohexen-1-ylboronic acid

Product 1

HCID 58994431[5-Amino-6-(4,4-dimethyl-cyclohex-1-enyl)-pyridin-2-yl]-acetic acid ethyl ester

Procedure

This compound was prepared from (5-nitro-pyridin-2-yl)-acetic acid ethyl ester (as prepared in the previous step) according to the procedure for nitro reduction and bromination in Example 33, step (b), followed by Suzuki coupling to 4,4-dimethyl-1-cyclohexen-1-ylboronic acid according to the procedure in Example 1, step (e). Mass spectrum (APCI, m/z): Calcd. for C17H24N2O2, 289.2 (M+H). found 289.2.

Workup

  1. customas prepared in the previous step)

Sources & evidence

ORD record
ord-7f6b85010b6c4dbbab9f7a5a471d5a94
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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