Potassium Carbonate → 5-(6-methoxy-2,3-dihydro-1H-inden-5-yl)pyridin-2-amine

HRID 874638Notes

Reaction equation

HRID 874638 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[CH2:7][CH2:6][CH2:5]2.FC1(F)OC2C=C(C)C(C3N=C[C:26]([NH:29][C:30](=O)[C:31]4[CH:36]=[CH:35]C=CC=4F)=[N:27]C=3)=CC=2O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(#N)C.O.ClCCl>[CH3:12][O:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][CH2:7]2)=[CH:3][C:2]=1[C:31]1[CH:36]=[CH:35][C:26]([NH2:27])=[N:29][CH:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 152482825-bromo-6-methoxy-2,3-dihydro-1H-indeneHCID 58486754N-(5-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)pyrazin-2-yl)-2-fluorobenzamide

Product 1

HCID 584872065-(6-methoxy-2,3-dihydro-1H-inden-5-yl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 67448433Dioxane acetonitrile waterSolvent

Conditions

Temperature
90 °C

Procedure

Palladium tetrakis-triphenylphosphine (25 mg, 20 μmol) was added to a degassed solution of bromide 125 (100 mg, 0.4 mmol) and boronate 11 (174 mg, 0.8 mmol) in dioxane:acetonitrile:water (9:9:2, 2.2 mL) and potassium carbonate (139 mg, 0.7 mmol). The resulting mixture was heated under argon at 90° C. with stirring for 2 days. The mixture was then cooled, diluted with dichloromethane (5 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 126 as an impure oil: LRESIMS m/z 241.1 [M+H]+, calcd. for C15H17N2O1 241.1.

Workup

  1. temperatureThe mixture was then cooled
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-556294e056354ed38bde9c8b96d0116c
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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