Potassium phosphate, tribasic, monohydrate → (5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine

HRID 2047152노트

반응식

HRID 2047152 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:5]2[N:25]=[CH:26][C:27](I)=[C:4]2[N:3]=1.[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:5]2[N:25]=[CH:26][C:27]([C:31]3[CH:30]=[N:29][C:38]4[C:33]([CH:32]=3)=[CH:34][CH:35]=[CH:36][CH:37]=4)=[C:4]2[N:3]=1

참가 물질

7

반응물 3

HCID 22031701Potassium phosphate, tribasic, monohydrateHCID 22173501Quinoline-2-boronic acidHCID 772312185-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

생성물 1

HCID 86664780(5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
60 °C

실험 절차

To crude 5-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (7.1 g) in DME (120 mL) and H2O (15 mL) was added the quinoline boronic acid (2.4 g, 14.1 mmol), PdCl2(dppf)2 (1.0 g, 1.2 mmol) and K3PO4.H2O (5.4 g, 25.6 mmol). The reaction mixture was heated at 60° C. for 2 hours, at which time LC/MS analysis confirmed full consumption of starting material. On cooling, H2O (40 mL) and EtOAc (100 mL) were added and organics were extracted with EtOAc (4×50 mL), dried (Na2SO4) and concentrated in vacuo to give a brown oil. Gradient column chromatography on silica eluting with 10% to 60% EtOAc/hexanes gave 5-chloro-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine as a light yellow solid (4.1 g, 7.4 mmol, 65% over three steps). LCMS: 2.62 mins, m/z=556.2 (MH+).

후처리

  1. customconsumption of starting material
  2. temperatureOn cooling
  3. additionH2O (40 mL) and EtOAc (100 mL) were added
  4. extractionorganics were extracted with EtOAc (4×50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto give a brown oil

출처 및 근거

ORD 기록
ord-e59ba2cf5d484c0298152712d59901b8
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08591943B2

반응 노트

불러오는 중…