3-Bromopyridine → HCID 67151979, compound

HRID 550572Notes

Reaction equation

HRID 550572 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].Br[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 122863-BromopyridineHCID 72669Methyl 3-aminopyrazinecarboxylateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 67151979HCID 67151979, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

3-Aminopyrazine-2-carboxylic acid methyl ester (0.8 g, 5.2 mmol) and 3-bromopyridine (1.2 g, 7.8 mmol) were dissolved in 20 mL dry toluene. 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.6 g, 1.04 mmol), sodium tert.-butylate (0.75 g, 7.8 mmol) and tri(dibenzylideneacetone)dipalladium chloroform complex (0.54 g, 0.52 mmol) were added and the reaction mixture was stirred under microwave irradiation for 60 minutes at 150° C. The reaction mixture was then evaporated and purified by flash chromatography on silica gel (heptane/ethyl acetate 1:2->0:100 gradient). The desired product was obtained as a brown solid (260 mg, 22%), MS: m/e=231.1 (M+H+).

Workup

  1. customThe reaction mixture was then evaporated
  2. custompurified by flash chromatography on silica gel (heptane/ethyl acetate 1:2->0:100 gradient)

Sources & evidence

ORD record
ord-bbb9ac32e34d4532a254858bfa96c1fb
Source dataset
uspto-grants-2011_05
Patent number
US07947685B2

Reaction notes

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