Pyridine → 2-(4-Chlorophenyl)-5-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)furo[3,2-c]pyridin-4(5H)-one

HRID 60377노트

반응식

HRID 60377 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][NH:12][C:11](=[O:17])[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[CH:18]1([C:21]2[N:22]=[C:23]3[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][N:24]3[C:32]=2[CH3:33])[CH2:20][CH2:19]1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][N:12]([C:26]4[CH:27]=[CH:28][C:23]5[N:24]([C:32]([CH3:33])=[C:21]([CH:18]6[CH2:20][CH2:19]6)[N:22]=5)[CH:25]=4)[C:11](=[O:17])[C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 580155582-(4-chlorophenyl)-5H-furo[3,2-c]pyridine-4-oneHCID 89690439HCID 89690439, 화합물

생성물 1

HCID 718165182-(4-Chlorophenyl)-5-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)furo[3,2-c]pyridin-4(5H)-one수율 5.9%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

A mixture of 2-(4-chlorophenyl)furo[3,2-c]pyridin-4(5H)-one (100 mg), (2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)boronic acid (106 mg), copper(II) acetate (4.99 mg), pyridine (0.066 mL), MS-4A (48.9 mg) and DMF (5.0 mL) was stirred at room temperature for 4 hr and at 50° C. overnight. After filtration of the obtained mixture through Celite, the filtrate was poured into 1 N hydrochloric acid and extracted with ethyl acetate. The obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo. The obtained solid was washed with ethanol to give the title compound (10.0 mg) as a pale brown solid.

후처리

  1. filtrationAfter filtration of the obtained mixture through Celite
  2. additionthe filtrate was poured into 1 N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. washThe obtained solid was washed with ethanol

출처 및 근거

ORD 기록
ord-2034a445db9f4e60aba5da68a027397c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440987B2

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