Sodium Bicarbonate → 3-Chloro-2-(4-chloro-2-fluoro-5-methoxyphenyl)-5-methylsulfinylpyridine

HRID 1279191Notes

Reaction equation

HRID 1279191 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([S:9]([CH3:11])=[O:10])=[CH:4][N:3]=1.[Cl:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][C:16](B(O)O)=[C:15]([F:24])[CH:14]=1.C(=O)([O-])O.[Na+]>O.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>[Cl:8][C:7]1[C:2]([C:16]2[CH:17]=[C:18]([O:19][CH3:20])[C:13]([Cl:12])=[CH:14][C:15]=2[F:24])=[N:3][CH:4]=[C:5]([S:9]([CH3:11])=[O:10])[CH:6]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 10932600(4-Chloro-2-fluoro-5-methoxyphenyl)boronic acidHCID 18427299HCID 18427299, compound

Product 1

HCID 184273013-Chloro-2-(4-chloro-2-fluoro-5-methoxyphenyl)-5-methylsulfinylpyridineYield 30.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

4.6 g of 2,3-dichloro-5-methylsulfinylpyridine, 4.5 g of 4-chloro-2-fluoro-5-methoxybenzeneboronic acid, 5.5 g of sodium hydrogen carbonate and 1.0 g of tetrakis(triphenylphosphine)palladium(0) were refluxed for 180 hours in a mixture of 100 ml of water and 100 ml of tetrahdyrofuran. After the tetrahydrofuran has been evaporated, the residue was extracted four times with in each case 70 ml of MTB. The combined organic phases were then dried over sodium sulfate and finally concentrated. The resulting oil was purified by means of chromatography on silica gel (eluent: cyclohexane/MTB=7:3→1:1 and cyclohexane/ethyl acetate=2:1). Stirring this purified oil with diethyl ether gave 2.2 g (30%) of white crystals.; m.p.: 117-118° C.

Workup

  1. customAfter the tetrahydrofuran has been evaporated
  2. extractionthe residue was extracted four times with in each case 70 ml of MTB
  3. dry with materialThe combined organic phases were then dried over sodium sulfate
  4. concentrationfinally concentrated
  5. customThe resulting oil was purified by means of chromatography on silica gel (eluent: cyclohexane/MTB=7:3→1:1 and cyclohexane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-e4fcd8c8d9eb4b449f8384805e5696e6
Source dataset
uspto-grants-2002_09
Patent number
US06448205B1

Reaction notes

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