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

HRID 1485147ノート

反応式

HRID 1485147 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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.

出典と根拠

ORDレコード
ord-6979a8a812004f9f8492668e2c4f1b4b
出典データセット
uspto-grants-2016_08
特許番号
US09421205B2

反応ノート

読み込み中…