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

HRID 336406Notes

Reaction equation

HRID 336406 reaction equation
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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-a2eeac91b4f04a35975b2331edd9176d
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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