Water → 2-{3-Fluoro-4-[(phenylmethyl)oxy]phenyl}-5-(methylsulfonyl)pyridine

HRID 423574Notes

Reaction equation

HRID 423574 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]([F:22])[CH:9]=2)=[N:6][CH:7]=1.[Na+].[CH3:24][S:25]([O-:27])=[O:26].[OH-].[Na+].O>CS(C)=O>[F:22][C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([S:25]([CH3:24])(=[O:27])=[O:26])=[CH:7][N:6]=2)[CH:13]=[CH:12][C:11]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2733271Sodium methanesulfinateHCID 666732465-Bromo-2-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}pyridine

Product 1

HCID 666731192-{3-Fluoro-4-[(phenylmethyl)oxy]phenyl}-5-(methylsulfonyl)pyridineYield 34%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-{3-Fluoro-4-[(phenylmethyl)oxy]phenyl}-5-(methylsulfonyl)pyridine (0.168 g, 34%) was prepared as a white solid from 5-bromo-2-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}pyridine (0.50 g, 1.40 mmol), methanesulfinic acid sodium salt (0.72 g, 80%, 5.58 mmol) Cul (0.80 g, 4.19 mmol), NaOH (67 mg, 1.68 mmol) and water (0.4 mL) in DMSO (15 mL) in a manner similar to Example 83, Step 2. The crude product was triturated with hot MeOH containing 5% of CHCl3. 1H NMR (400 MHz, CDCl3): δ 9.14 (d, 1H, J=2.4 Hz), 8.22 (dd, 1H, Ja=8.3 Hz, Jb=2.5 Hz), 7.91 (d, 1H, J=2.2 Hz), 7.90-7.70 (m, 2H), 7.50-7.30 (m, 5H), 7.11 (t, 1H, J=8.6 Hz), 5.23 (s, 2H), 3.13 (s, 3H); LRMS (ESI), m/z 358 (M+H).

Workup

  1. customThe crude product was triturated with hot MeOH containing 5% of CHCl3

Sources & evidence

ORD record
ord-c7c6ca5bac824cf5b05f95ec019bc913
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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