Hydrochloric Acid → HCID 16412784, compound

HRID 1276072Notes

Reaction equation

HRID 1276072 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])O.[Na+].Cl>O1CCCC1.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:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 201262(4-Methoxyphenyl)boronic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 16412784HCID 16412784, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

20.4 g of 2,3-dichloro-5-trifluoromethylpyridine, 18.9 g of p-methoxyphenylboronic acid, 0.4 g of tetrakis(triphenylphosphine)palladium(0) and 23.8 g of sodium hydrogencarbonate were refluxed for 2 hours in a mixture of 300 ml of tetrahydrofuran and 300 ml of water. After colling, the mixture was acidified by means of 10% strength hydrochloric acid. The tetrahydrofuran was removed by distillation under reduced pressure, and the product was then extracted three times with 100 m of methylene chloride in each case. The combined organic phases were sucked through silica gel and then evaporated. Recrystallization of the crude product from n-hexane gave 19.5 g (72%) of colorless crystals; m.p. 71-72° C.

Workup

  1. customThe tetrahydrofuran was removed by distillation under reduced pressure
  2. extractionthe product was then extracted three times with 100 m of methylene chloride in each case
  3. customevaporated
  4. customRecrystallization of the crude product from n-hexane

Sources & evidence

ORD record
ord-23a08c14fae64709990e4338657432ac
Source dataset
uspto-grants-2000_12
Patent number
US06165941

Reaction notes

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