Cesium carbonate → 3-(6-Methoxypyridin-3-yl)-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine

HRID 573327노트

반응식

HRID 573327 반응식
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]([CH:11]([CH3:13])[CH3:12])[N:3]=1.[CH3:14][O:15][C:16]1[N:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:14][O:15][C:16]1[N:21]=[CH:20][C:19]([C:2]2[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:5]3[N:4]([CH:11]([CH3:13])[CH3:12])[N:3]=2)=[CH:18][CH:17]=1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 667280773-bromo-1-isopropyl-1H-pyrazolo[4,3-b]pyridine

생성물 1

HCID 866889833-(6-Methoxypyridin-3-yl)-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine수율 89.5%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 3-bromo-1-isopropyl-1H-pyrazolo[4,3-b]pyridine (100 mg), 6-methoxypyridin-3-ylboronic acid (96 mg), Pd(OAc)2 (9.35 mg), and Xphos (39.7 mg) in THF (3 mL) was added a solution of Cs2CO3 (271 mg) in H2O (1 mL). The mixture was exposed to microwave irradiation at 100° C. for 30 min, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (100 mg).

후처리

  1. customirradiation at 100° C. for 30 min
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

출처 및 근거

ORD 기록
ord-c29caf5e70834c1f875e77dac3301b47
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029536B2

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