Toluene → N-{6-[3-(pyridin-3-ylamino)phenoxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide

HRID 1874557

反応式

HRID 1874557 の反応式
[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:26]=[N:27][CH:28]=[CH:29][CH:30]=1.CC(C)([O-])C.[K+].C1(C)C=CC=CC=1>C(=O)([O-])O.[Na+]>[N:27]1[CH:28]=[CH:29][CH:30]=[C:25]([NH:1][C:2]2[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=2)[O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]4[CH2:20][CH2:19]4)=[O:17])[N:14]=3)[CH:11]=2)[CH:26]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 122863-BromopyridineHCID 23665647Potassium tert-butoxideHCID 57749361N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

生成物 1

HCID 57749199N-{6-[3-(pyridin-3-ylamino)phenoxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide収率 12%

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
120 °C

実験手順

A mixture of N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (20.0 mg, 0.065 mmol), 3-bromopyridine (14.4 mg, 0.091 mmol), tris(dibenzylideneacetone)2 palladium(0) (6.8 mg, 0.0074 mmol), 5-bis(diphenylphosphino)-9,9-dimethylxanthene (4.3 mg, 0.007 mmol), potassium t-butoxide (17.2 mg, 0.153 mmol) and toluene (2.0 mL) was stirred at 120° C. for 13 hr. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by preparative HPLC to give the title compound (3.0 mg, 12%).

後処理

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

出典と根拠

ORDレコード
ord-0f688638b5fb45d78e58eb40a6e66ec0
出典データセット
uspto-grants-2012_11
特許番号
US08304557B2

関連ノート

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