5-Fluoro-4-methoxy-2-methylphenylboronic acid → 2-Benzyloxy-4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridine

HRID 1831544Notes

Reaction equation

HRID 1831544 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.[F:19][C:20]1[C:21]([O:30][CH3:31])=[CH:22][C:23]([CH3:29])=[C:24](B(O)O)[CH:25]=1>>[CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([C:24]2[CH:25]=[C:20]([F:19])[C:21]([O:30][CH3:31])=[CH:22][C:23]=2[CH3:29])[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 220216925-Fluoro-4-methoxy-2-methylphenylboronic acidHCID 220520652-(Benzyloxy)-4-chloro-3-nitropyridine

Product 1

HCID 220521462-Benzyloxy-4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridineYield 83%

Procedure

2-Benzyloxy-4-chloro-3-nitro-pyridine (Wilde, et. al. WO 99/01454) (1.0 g, 3.78 mmol) and 5-fluoro-4-methoxy-2-methyl-phenylboronic acid (prepared substantially as described in Speicher, A.; Kolz, J.; Sambanje, R. P. Synthesis, 2002, 17, 2503, which is incorporated herein by reference) (1.2 mg, 5.67 mmol) were treated substantially as described in Part A of Example 19a to give 1.15 g (83%) of 2-benzyloxy-4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridine: MS (EI) m/z 369.3 [(M+H)+, 100].

Workup

  1. customSynthesis, 2002, 17, 2503, which
  2. additionwere treated substantially

Sources & evidence

ORD record
ord-b6d132d12b2748f1b0146d3d1a368aa2
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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