(2-Chloro-4-(difluoromethoxy)phenyl)boronic acid → 2-Benzyloxy-4-(2-chloro-4-difluoromethoxy-phenyl)-3-nitro-pyridine

HRID 1831555Notes

Reaction equation

HRID 1831555 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]([O:26][CH:27]([F:29])[F:28])[CH:23]=[CH:22][C:21]=1B(O)O>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([C:21]2[CH:22]=[CH:23][C:24]([O:26][CH:27]([F:28])[F:29])=[CH:25][C:20]=2[Cl:19])[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 22052056(2-Chloro-4-(difluoromethoxy)phenyl)boronic acidHCID 220520652-(Benzyloxy)-4-chloro-3-nitropyridine

Product 1

HCID 220520472-Benzyloxy-4-(2-chloro-4-difluoromethoxy-phenyl)-3-nitro-pyridineYield 70%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

To a solution of 2-benzyloxy-4-chloro-3-nitro-pyridine (Wilde, et al. WO 99/01454, which is incorporated herein by reference) (5.0 g, 18.9 mmol) in DME/H2O, was added 2-chloro-4-difluoromethoxy-phenylboronic acid (Wilde, et al. WO 99/01454, which is incorporated by reference herein in its entirety) (4.20 g, 18.9 mmol), Ba(OH)2 8H2O (5.96 g, 18.9 mmol), and Pd(PPh3)2Cl2 (0.769 g, 1.10 mmol) were treated as in Part A of Example 113 to give 5.40 g (70%) of 2-benzyloxy-4-(2-chloro-4-difluoromethoxy-phenyl)-3-nitro-pyridine as a viscous oil. The crude intermediate was used in the following step.

Workup

  1. additionwere treated as in Part A of Example 113

Sources & evidence

ORD record
ord-d1fedadca59647138bc4d49bbe0d66ba
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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