2-(Benzyloxy)-4-chloro-3-nitropyridine → 2-Benzyloxy-4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridine

HRID 1831592Notes

Reaction equation

HRID 1831592 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]([N:26]([CH3:28])[CH3:27])[C:23]([F:29])=[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]([F:29])[C:24]([N:26]([CH3:27])[CH3:28])=[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

3

Reactant 2

HCID 220520652-(Benzyloxy)-4-chloro-3-nitropyridineHCID 220521252-Chloro-4-dimethylamino-5-fluorophenylboronic acid

Product 1

HCID 220521852-Benzyloxy-4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridineYield 59%

Procedure

2-Benzyloxy-4-chloro-3-nitro-pyridine (Wilde, et. al. WO 99/01454) (800 mg, 3.02 mmol) and 2-chloro-4-dimethylamino-5-fluorophenylboronic acid (Example B) (854 mg, 3.93 mmol) were treated substantially as described in Part A of Example 19a to give 715 mg (59%) of 2-benzyloxy-4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridine: 1H NMR (400 MHz, CDCl3) δ ppm 8.27 (d, J=5.4 Hz, 1 H), 7.45–7.43 (m, 2H), 7.40–7.29 (m, 3H), 6.93 (d, J=5.4 Hz, 1 H), 6.89 (d, J=13.2 Hz, 1 H), 6.85 (d, J=8.0 Hz, 1 H), 5.53 (s, 2 H), 2.91 (d, J=1.2 Hz, 6 H).

Sources & evidence

ORD record
ord-718967cdf0c74e30a6b78193ede5dc4d
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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