(5-Chloro-4-methoxy-2-methylphenyl)boronic acid → 2-Benzyloxy-4-(5-chloro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridine

HRID 1831578Notes

Reaction equation

HRID 1831578 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.[CH3:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([Cl:28])=[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:21]2[CH:22]=[C:23]([Cl:28])[C:24]([O:26][CH3:27])=[CH:25][C:20]=2[CH3:19])[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 11390036(5-Chloro-4-methoxy-2-methylphenyl)boronic acidHCID 220520652-(Benzyloxy)-4-chloro-3-nitropyridine

Product 1

HCID 220520712-Benzyloxy-4-(5-chloro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridineYield 47%

Procedure

2-Benzyloxy-4-chloro-3-nitro-pyridine (Wilde, et. al. WO 99/01454) (774 mg, 2.81 mmol) and 2-methyl-5-chloro-4-methoxyphenylboronic acid (prepared as described in Speicher, A.; Kolz, J.; Sambanje, R. P. Synthesis, 2002, 17, 2503) (620 mg, 3.09 mmol) were treated substantially as described in Part A of Example 19a to give 1.15 g (47%) of 2-benzyloxy-4-(5-chloro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridine: 1H NMR (400 MHz, CDCl3) δ ppm 8.26 (d, J=5.1 Hz, 1 H), 7.45–7.42 (m, 2H), 7.39–7.30 (m, 3H), 7.13 (s, 1H), 6.82 (d, J=5.1 Hz, 1 H), 6.79 (s, 1 H), 5.54 (s, 2 H), 3.90 (s, 3H), 2.14 (s, 3H).

Workup

  1. customSynthesis, 2002, 17, 2503) (620 mg, 3.09 mmol)
  2. additionwere treated substantially

Sources & evidence

ORD record
ord-a1243a8ee7be416ca829b99544225ed2
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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