Triphenylphosphine → tert-Butyl 3-((2-(methylthio)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)benzoate

HRID 1473030노트

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HRID 1473030 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])#[CH:2].I[C:17]1[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][N:20]=[C:19]([S:27][CH3:28])[N:18]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:28][S:27][C:19]1[N:18]=[C:17]([C:2]#[C:1][C:3]2[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=2)[C:6]([O:8][C:9]([CH3:11])([CH3:12])[CH3:10])=[O:7])[C:22]([C:23]([F:26])([F:24])[F:25])=[CH:21][N:20]=1

참가 물질

6

반응물 3

HCID 11776TriphenylphosphineHCID 717433934-Iodo-2-(methylthio)-5-(trifluoromethyl)pyrimidineHCID 71743555Tert-butyl 3-ethynylbenzoate

생성물 1

HCID 71217514tert-Butyl 3-((2-(methylthio)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)benzoate

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

t-Butyl 3-ethynylbenzoate (I17) (1.603 g, 7.93 mmol), 4-iodo-2-(methylthio)-5-(trifluoromethyl)pyrimidine (I14) (1.647 g, 5.15 mmol), PdCl2(PPh3)2 (0.316 g, 0.45 mmol), PPh3 (0.355 g, 1.35 mmol), Cu(I)I (0.232 g, 1.22 mmol) and trethylamine (4.00 mL, 28.7 mmol) were combined in DMF (20 mL) and the resulting mixture heated at 120° C. under microwave irradiation for 25 minutes. The mixture was then concentrated under reduced pressure and purified twice using silica gel column chromatography (10-20% EtOAc/petroleum benzine 40-60° C. then 50-100% DCM/petroleum benzine 40-60° C.) to give the title compound (I18) (0.624 g, 31%) as a yellow solid; 1H NMR (400 MHz, CDCl3) δ 8.73 (d, J=0.8 Hz, 1H), 8.25 (m, 1H), 8.08 (m, 1H), 7.78 (m, 1H), 7.48 (m, 1H), 2.63 (s, 3H), 1.61 (s, 9H).

후처리

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. custompurified twice using silica gel column chromatography (10-20% EtOAc/petroleum benzine 40-60° C.

출처 및 근거

ORD 기록
ord-39209b54b4fb4e328f6524c5b8c22088
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012461B2

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