Potassium Carbonate → 3-(1-Phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-one

HRID 1014717

반응식

HRID 1014717 반응식
[N+:1]([C:4]1[C:5]([NH:20][CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])=[N:6][C:7]([C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][CH:14]=[N:15]3)=[CH:8][CH:9]=1)([O-])=O.ClC1N=C(NC(C2C=CC=CC=2)C)C([N+]([O-])=O)=CC=1.N1C2C(=C(B(O)O)C=CC=2)C=CC=1.[C:61](=O)([O-])[O-:62].[K+].[K+]>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:23]1([CH:21]([N:20]2[C:5]3=[N:6][C:7]([C:10]4[CH:19]=[CH:18][CH:17]=[C:16]5[C:11]=4[CH:12]=[CH:13][CH:14]=[N:15]5)=[CH:8][CH:9]=[C:4]3[NH:1][C:61]2=[O:62])[CH3:22])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 5153389Quinolin-5-ylboronic acidHCID 433303216-chloro-3-nitro-N-(1-phenylethyl)pyridin-2-amineHCID 666998813-Nitro-N-(1-phenylethyl)-6-(quinolin-5-yl)pyridin-2-amine

생성물 1

HCID 249846803-(1-Phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-one수율 79%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

3-Nitro-N-(1-phenylethyl)-6-(quinolin-5-yl)pyridin-2-amine. To a solution of 6-chloro-3-nitro-N-(1-phenylethyl)pyridin-2-amine (2.24 g, 8.07 mmol) and quinolin-5-ylboronic acid (1.81 g, 10.5 mmol) in DMF (150 mL) was added potassium carbonate (4.46 g, 32.3 mmol) in water (25 mL). The reaction solution was purged with a stream of nitrogen followed by the addition of tetrakis(triphenylphosphine)palladium(0) (932 mg, 0.81 mmol). After heating at 85° C. for 2 h, the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography to afford the title compound (2.36 g, 79% yield). MS (ESI) m/z 371.3 [M+1]+.

후처리

  1. customThe reaction solution was purged with a stream of nitrogen
  2. customthe solvent was removed under reduced pressure
  3. customThe crude product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-fcf5d008b09942b1a76cd25daa858666
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981893B2

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