홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Potassium Phosphate, Tribasic → 7-((2-Cyclopropylpyrimidin-5-yl)methyl)-4-(1-methyl-1H-pyrazol-4-yl)quinoline-2-carbonitrile

HRID 922789
노트
인쇄 미리보기

반응식

HRID 922789 반응식
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](Cl)=[CH:8][C:9]([C:13]#[N:14])=[N:10]2)=[CH:5][CH:4]=1.[CH:16]1([C:19]2[N:24]=[CH:23][C:22](B3OC(C)(C)C(C)(C)O3)=[CH:21][N:20]=2)[CH2:18][CH2:17]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:42][N:43]1[CH:47]=[C:46](B2OC(C)(C)C(C)(C)O2)[CH:45]=[N:44]1>O1CCOCC1.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].C(Cl)Cl>[CH:16]1([C:19]2[N:20]=[CH:21][C:22]([CH2:2][C:3]3[CH:12]=[C:11]4[C:6]([C:7]([C:46]5[CH:45]=[N:44][N:43]([CH3:42])[CH:47]=5)=[CH:8][C:9]([C:13]#[N:14])=[N:10]4)=[CH:5][CH:4]=3)=[CH:23][N:24]=2)[CH2:17][CH2:18]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 457872832-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidineHCID 667895247-(Bromomethyl)-4-chloroquinoline-2-carbonitrile

생성물 1

HCID 715661297-((2-Cyclopropylpyrimidin-5-yl)methyl)-4-(1-methyl-1H-pyrazol-4-yl)quinoline-2-carbonitrile
수율 77%

시약·촉매·용매 3

HCID 178418807HCID 178418807, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

After degassing with N2, a mixture of 7-(bromomethyl)-4-chloroquinoline-2-carbonitrile (2-4, 650 mg, 2.31 mmol), 2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (580 mg, 2.36 mmol), Pd(dppf)Cl2—CH2Cl2 adduct (94 mg, 0.11 mmol), and K3PO4 (1960 mg, 9.24 mmol) in 1,4-dioxane (13.7 mL) and H2O (1.7 mL) was heated at 100° C. for 30 min under microwave condition. The mixture was cooled to room temperature, and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (528 mg, 2.54 mmol) was added. After degassing with N2, the mixture was then heated at 115° C. for 30 min under microwave condition. The reaction mixture was cooled, diluted with H2O (10 mL) and the mixture was extracted with ethyl acetate (2×50 mL). The combined organic fractions were washed with brine, dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with EtOAc/Hexane (0-100%) to afford 7-((2-cyclopropylpyrimidin-5-yl)methyl)-4-(1-methyl-1H-pyrazol-4-yl)quinoline-2-carbonitrile (6-1, 649 mg, 77%). LRMS m/z (M+H)+ 367.3 found, 367.2 required.

후처리

  1. customAfter degassing with N2
  2. temperatureThe mixture was cooled to room temperature
  3. customAfter degassing with N2
  4. temperaturethe mixture was then heated at 115° C. for 30 min under microwave condition
  5. temperatureThe reaction mixture was cooled
  6. additiondiluted with H2O (10 mL)
  7. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  8. washThe combined organic fractions were washed with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. customthe solvent was evaporated under reduced pressure
  12. customThe crude product was purified by column chromatography on silica gel
  13. washeluting with EtOAc/Hexane (0-100%)

출처 및 근거

ORD 기록
ord-f1d466450eee417b9b29893b1cf65528
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09278960B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트