Ethanol → HCID 68065989, 화합물

HRID 594946노트

반응식

HRID 594946 반응식
I[C:2]1[C:6]2[CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:5]=2[N:4](C(OCC)=O)[N:3]=1.[N:23]1[CH:24]=[CH:25][N:26]2[CH:31]=[C:30](B(O)O)[CH:29]=[CH:28][C:27]=12.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[N:23]1[CH:24]=[CH:25][N:26]2[CH:31]=[C:30]([C:2]3[C:6]4[CH2:7][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:9][CH2:10][C:5]=4[NH:4][N:3]=3)[CH:29]=[CH:28][C:27]=12

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 103648605-tert-Butyl 1-ethyl 3-iodo-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-1,5(4H)-dicarboxylateHCID 44119340Imidazo[1,2-a]pyridine-6-boronic acid

생성물 1

HCID 68065989HCID 68065989, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

반응 조건

온도
160 °C

실험 절차

5-Tert-butyl 1-ethyl 3-iodo-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-1,5(4H)-dicarboxylate (1 g, 0.002 mol), (synthesized from patent procedure: WO 2004014374 A1) was added to a vial containing imidazo[1,2-a]pyridin-6-ylboronic acid (0.577 g, 0.00356 mol) and tetrakis(triphenylphosphine)palladium (0.1372 g, 0.00011 mol). After purging the vial with nitrogen gas, dioxane: ethanol: water solution (7:3:2, 7.125 mL) and 2M sodium carbonate (0.007125 mol) was added to the vial respectively. The reaction mixture was stirred and was heated in the microwave at 160° C. for 20 min. Upon completion, the mixture was concentrated under vacuo. The residue was dissolved in ethyl acetate, and filtered through a fitted reservoir. The ethyl acetate layer was concentrated and columned using flash chromatography (0-100% ethyl acetate in hexane and 0-20% methanol in dichloromethane. The remaining residue that didn't dissolve in ethyl acetate was dissolved in methanol and filtered through a fritted reservoir. The methanol layer was concentrated and submitted for reverse phase prep. Pure product (quantitative yield) was recovered.

후처리

  1. additionwas added to
  2. customAfter purging the vial with nitrogen gas, dioxane
  3. concentrationUpon completion, the mixture was concentrated under vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. filtrationfiltered through a fitted reservoir
  6. concentrationThe ethyl acetate layer was concentrated
  7. dissolutionThe remaining residue that didn't dissolve in ethyl acetate
  8. dissolutionwas dissolved in methanol
  9. filtrationfiltered through a fritted reservoir
  10. concentrationThe methanol layer was concentrated

출처 및 근거

ORD 기록
ord-c9bca231b92d417299d21605fe2d1365
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242981B2

반응 노트

불러오는 중…