Potassium Phosphate, Tribasic → 1-(5-(3-(Trifluoromethyl)phenyl)pyrimidin-2-yl)ethanone

HRID 57395

반응식

HRID 57395 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[F:11][C:12]([F:23])([F:22])[C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN(C1C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=CC=1)C>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[C:17]([C:2]2[CH:3]=[N:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=2)[CH:16]=[CH:15][CH:14]=1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 534880641-(5-Bromopyrimidin-2-yl)ethan-1-one

생성물 1

HCID 867301721-(5-(3-(Trifluoromethyl)phenyl)pyrimidin-2-yl)ethanone수율 65.5%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

A cloudy solution of 1-(5-bromopyrimidin-2-yl)ethanone (300 mg, 1.49 mmol), 3-(trifluoromethyl)phenylboronic acid (567 mg, 2.98 mmol), K3PO4 (950 mg, 4.48 mmol), DavePhos ligand [2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl](59 mg, 0.15 mmol), and Pd(OAc)2 (17 mg, 0.075 mmol) in 6 mL toluene was heated at 100° C. for 1 h. The mixture was cooled to room temperature, and filtered through Celite. Filter cake was rinsed with 30 mL EtOAc. The filtrate was poured into 20 mL water. Layers were separated, and the aqueous was further extracted with EtOAc (20 mL). Combined organics were washed with water (20 mL) and brine (20 mL), dried over Na2SO4, filtered and concentrated directly onto silica gel. Column chromatography (10-100% EtOAc/heptane) gave 0.26 g 1-(5-(3-(trifluoromethyl)phenyl)pyrimidin-2-yl)ethanone as tan solid. MS m/z 267.1 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 9.16 (s, 2H), 7.93-7.69 (m, 4H), 2.87 (s, 3H).

후처리

  1. filtrationfiltered through Celite
  2. filtrationFilter cake
  3. washwas rinsed with 30 mL EtOAc
  4. additionThe filtrate was poured into 20 mL water
  5. customLayers were separated
  6. extractionthe aqueous was further extracted with EtOAc (20 mL)
  7. washCombined organics were washed with water (20 mL) and brine (20 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated directly onto silica gel

출처 및 근거

ORD 기록
ord-1308a2f6995e48148fcbb0c8db6844bd
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434719B2

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