(2,4-Dichlorophenyl)boronic acid → 2-(Benzyloxy)-4-(2,4-dichlorophenyl)-3-nitropyridine

HRID 1831501Notes

Reaction equation

HRID 1831501 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13](Cl)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1B(O)O>>[CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([C:23]2[CH:22]=[CH:21][C:20]([Cl:19])=[CH:25][C:24]=2[Cl:26])[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 220520652-(Benzyloxy)-4-chloro-3-nitropyridine

Product 1

HCID 220521282-(Benzyloxy)-4-(2,4-dichlorophenyl)-3-nitropyridineYield 51%

Procedure

2-Benzyloxy-4-chloro-3-nitro-pyridine (Wilde, et. al. WO 99/01454, which is incorporated herein by reference in its entirety) (11 g, 41.6 mmol) and 2,4-dichlorophenylboronic acid (11.9 g, 62.3 mmol) were treated substantially as described in Part A of Example 19a to give 8.0 g (51%) of 2-benzyloxy-4-(2,4-dichloro-phenyl)-3-nitro-pyridine: MS (AP) m/z 375.2 [(M+H)+, 100].

Workup

  1. additionwere treated substantially

Sources & evidence

ORD record
ord-b229515c89af43d9ab83aaef56367a25
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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