Cesium carbonate → 5-(4-(Morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 336406

반응식

HRID 336406 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:21]=[CH:20][C:12]([CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=2)O1.Br[C:24]1[N:29]2[N:30]=[C:31]([NH2:33])[N:32]=[C:28]2[CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(COC)OC.O>C(OCC)(=O)C.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]>[O:17]1[CH2:16][CH2:15][N:14]([CH2:13][C:12]2[CH:11]=[CH:10][C:9]([C:24]3[N:29]4[N:30]=[C:31]([NH2:33])[N:32]=[C:28]4[CH:27]=[CH:26][CH:25]=3)=[CH:21][CH:20]=2)[CH2:19][CH2:18]1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 27955024-((Morpholino)methyl)phenylboronic acid pinacol esterHCID 18180031Water 1,2-dimethoxyethaneHCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

생성물 1

HCID 591864835-(4-(Morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine수율 69%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine (1.9 g, 6.3 mmol), 5-bromo-[1,2,4]triazolo[1,5-a]pyridine-2-amine (1 g, 5 mmol), 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride (250 mg, 0.63 mmol), and cesium carbonate (4.1 g, 12.6 mmol) in 10:1 dimethoxyethane/water (11 mL) was heated at 140° C. under microwave radiation for 1 h. The reaction mixture was diluted with ethyl acetate (200 mL), and the resulting suspension was filtered through celite. The filtrate was concentrated, and the resulting residue was purified by flash column chromatography (petroleum ether→ethyl acetate) to provide product (1 g, 69% yield). LCMS (ESI) m/z: 310.

후처리

  1. filtrationthe resulting suspension was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. customthe resulting residue was purified by flash column chromatography (petroleum ether→ethyl acetate)

출처 및 근거

ORD 기록
ord-a2eeac91b4f04a35975b2331edd9176d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889673B2

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