Potassium Carbonate → 3-(2-Bromo-5-(trifluoromethyl)phenyl)pyridine

HRID 1473366노트

반응식

HRID 1473366 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1I.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:15]1[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=1

참가 물질

7

반응물 3

HCID 11430Potassium Carbonate2회HCID 27343783-Pyridinylboronic acid2회HCID 467352311-Bromo-2-iodo-4-(trifluoromethyl)benzene

생성물 1

HCID 866874133-(2-Bromo-5-(trifluoromethyl)phenyl)pyridine수율 69.8%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

A solution of Pd(Ph3P)4 (1.410 g, 1.220 mmol), 1-bromo-2-iodo-4-(trifluoromethyl)benzene (3.94 ml, 24.41 mmol), pyridin-3-ylboronic acid (3.00 g, 24.41 mmol), and potassium carbonate (13.49 g, 98 mmol) in 32 mL dioxane and 16 mL water was heated to 120° C. overnight. LC/MS showed incomplete conversion, so an additional portion of pyridin-3-ylboronic acid (3.00 g, 24.41 mmol) and potassium carbonate (13.49 g, 98 mmol) were added and the reaction mixture was heated to 120° C. for 3 hours. LC/MS showed no further conversion, so the reaction mixture was poured into water and was extracted with DCM. The organics were then concentrated. Purification of the crude residue by column chromatography (0-100% EtOAc/heptane) gave 3-(2-bromo-5-(trifluoromethyl)phenyl)pyridine (5.150 g, 17.05 mmol, 69.8% yield) as a yellow solid. m/z (ESI) 303.9 (M+H)+.

후처리

  1. extractionwas extracted with DCM
  2. concentrationThe organics were then concentrated
  3. customPurification of the crude residue by column chromatography (0-100% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-e6982e0c289148e2ab638a8b576b335c
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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