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

HRID 1874557

반응식

HRID 1874557 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

반응 조건

온도
120 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-0f688638b5fb45d78e58eb40a6e66ec0
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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