Toluene → HCID 57749220, compound

HRID 1874556Notes

Reaction equation

HRID 1874556 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[CH:11]=1.Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.CC(C)([O-])C.[K+].C1(C)C=CC=CC=1>C(=O)(O)[O-].[Na+]>[N:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[NH:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 79732-BromopyridineHCID 23665647Potassium tert-butoxideHCID 57749361N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749220HCID 57749220, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (19.7 mg, 0.064 mmol), 2-bromopyridine (15.4 mg, 0.098 mmol), tris(dibenzylideneacetone)2 palladium(0) (6.1 mg, 0.007 mmol), 5-bis(diphenylphosphino)-9,9-dimethylxanthene (3.9 mg, 0.007 mmol), potassium t-butoxide (18.1 mg, 0.161 mmol) and toluene (4.0 mL) was stirred at 120° C. for 15 hr. The reaction mixture was diluted with aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by preparative HPLC to give the title compound (9.9 mg, 40%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-d8920791e7f94dbb815af0b8a22a4f84
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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