Potassium Fluoride → 3'-Chloro-4'-methoxy-6-trifluoromethyl-biphenyl-3-carboxylic Acid

HRID 1475731

반응식

HRID 1475731 반응식
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6].[Cl:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Cl:15][C:16]1[CH:17]=[C:18]([C:2]2[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

참가 물질

7

반응물 4

HCID 522689Potassium FluorideHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 32475223-Chloro-4-methoxybenzeneboronic acidHCID 223375703-Bromo-4-(trifluoromethyl)benzoic acid

생성물 1

HCID 671701033'-Chloro-4'-methoxy-6-trifluoromethyl-biphenyl-3-carboxylic Acid

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

반응 조건

온도
50 °C

실험 절차

3-Bromo-4-trifluoromethyl-benzoic acid (0.484 g, 1.80 mmol), 3-chloro-4-methoxyphenylboronic acid (0.503 g, 2.70 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.313 g, 1.08 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.494 g, 0.54 mmol) and potassium fluoride (0.345 g, 5.93 mmol) were weighed into a flask and dioxane (10 ml) was added under argon, and the mixture was stirred for 24 h at 50° C. The mixture was filtered over celite and evaporated to dryness. The residue was purified by preparative RP HPLC (water/ACN gradient) to yield the title compound.

후처리

  1. filtrationThe mixture was filtered over celite
  2. customevaporated to dryness
  3. customThe residue was purified by preparative RP HPLC (water/ACN gradient)

출처 및 근거

ORD 기록
ord-c04dae48045b4649b9170de709fa5306
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018383B2

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