Sodium Carbonate → 4-(6-(Methylsulfonyl)pyridin-3-yl)phenol

HRID 423516Notes

Reaction equation

HRID 423516 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:13]=[CH:14][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[N:16][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:21][S:18]([C:15]1[N:16]=[CH:17][C:12]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 134334245-Bromo-2-methanesulfonylpyridine

Product 1

HCID 574579804-(6-(Methylsulfonyl)pyridin-3-yl)phenolYield 79%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-[6-(Methylsulfonyl)-3-pyridinyl]phenol was prepared as a brown solid from (4-hydroxyphenyl)boronic acid (0.34 g, 2.40 mmol), 5-bromo-2-(methylsulfonyl)pyridine (0.54 g, 2.29 mmol), 2M Na2CO3 (15 mL) and Pd(PPh3)4 (25 mg, 0.02 mmol) in DME (5 mL) in a manner similar to Example 1, Step 1. The crude product was triturated with 1:1 CH2Cl2/hexane to give 0.45 g (79%) of 4-[6-(methylsulfonyl)-3-pyridinyl]phenol as a brown solid. 1H NMR (400 MHz, DMSO-d6): δ 9.88 (s, 1H), 9.01 (d, 1H, J=2.2 Hz), 8.30 (dd, 1H, Ja=8.3 Hz, Jb=2.2 Hz), 8.02 (d, 1H, J=8.3 Hz), 7.66 (d, 2H, J=8.8 Hz), 6.90 (d, 2H, J=8.5 Hz), 3.27 (s, 3H); LRMS (APCI), m/z 250 (M+H).

Workup

  1. customThe crude product was triturated with 1:1 CH2Cl2/hexane

Sources & evidence

ORD record
ord-26e1c75a8eb64c1281fc52ed4fe5c801
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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