Sodium Carbonate → 3-Pyridinol, 6-[4-[(1-methylethyl)sulfonyl]phenyl]-

HRID 423549Notes

Reaction equation

HRID 423549 reaction equation
[CH3:1][CH:2]([S:4]([C:7]1[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:3].Br[C:17]1[N:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC>[CH3:1][CH:2]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:17]2[N:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:3]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27628652-Bromo-5-hydroxypyridineHCID 441193274-(Isopropylsulphonyl)benzeneboronic acid

Product 1

HCID 666732583-Pyridinol, 6-[4-[(1-methylethyl)sulfonyl]phenyl]-Yield 29.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

6-{4-[(1-Methylethyl)sulfonyl]phenyl}-3-pyridinol (0.47 g, 29%) was prepared as a tan solid from {4-[(1-methylethyl)sulfonyl]phenyl}boronic acid (1.97 g, 8.62 mmol), 6-bromo-3-pyridinol (1 g, 5.75 mmol), Pd(PPh3)2Cl2 (200 mg, 0.28 mmol), 2M Na2CO3 (5 mL) and DME (5 mL) in a manner similar to Example 21, Step 3. The material was purified by chromatography on a silica gel column eluted with 0 to 5% MeOH/CH2Cl2. 1H NMR (400 MHz, CDCl3): δ 8.36 (d, 1H, J=2.9 Hz), 8.06 (d, 2H, J=8.6 Hz), 7.93 (d, 2H, J=8.6 Hz), 7.68 (d, 1H, J=8.8 Hz), 7.30 (dd, 1H, Ja=8.8 Hz, Jb=2.9 Hz), 3.32-3.16 (m, 1H), 1.30 (d, 6H, J=6.9 Hz); LRMS (ESI), m/z 276 (M−H).

Workup

  1. customThe material was purified by chromatography on a silica gel column
  2. washeluted with 0 to 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-f11593b85fd44798ac9e706ba8daecff
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

Loading…