3-Bromo-5-ethoxy-4-hydroxybenzaldehyde → 4-(2-Amino-pyridin-3-ylmethoxy)-3-bromo-5-ethoxy-benzaldehyde

HRID 910751Notes

Reaction equation

HRID 910751 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH2:12][CH3:13])[C:9]=1[OH:10])[CH:5]=[O:6].[NH2:14][C:15]1[C:20]([CH2:21]O)=[CH:19][CH:18]=[CH:17][N:16]=1>>[NH2:14][C:15]1[C:20]([CH2:21][O:10][C:9]2[C:8]([O:11][CH2:12][CH3:13])=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=2[Br:1])=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

3

Reactant 2

HCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehydeHCID 11159325(2-Aminopyridin-3-yl)methanol

Product 1

HCID 866244114-(2-Amino-pyridin-3-ylmethoxy)-3-bromo-5-ethoxy-benzaldehyde

Procedure

Mitsunobu reaction of 3-bromo-5-ethoxy-4-hydroxy benzaldehyde (490 mg) with (2-amino-pyridin-3-yl)-methanol (250 mg) was preformed according to the method described for example 21d. The residue was chromatographed on silica gel in dichloromethane/methanol=99/1 (v/v) as eluent. Yield: 500 mg. MS-ESI: [M+H]+=351/353.

Workup

  1. customThe residue was chromatographed on silica gel in dichloromethane/methanol=99/1 (v/v) as eluent

Sources & evidence

ORD record
ord-cc0a08cc8b2b433fadb01ceb96f0e026
Source dataset
uspto-grants-2011_09
Patent number
US08022218B2

Reaction notes

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