Aniline → HCID 70670709, 화합물

HRID 1894978노트

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HRID 1894978 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5]2.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:17]1([NH:16][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5]3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

7

반응물 4

HCID 6115AnilineHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 53465709Methyl 6-bromoquinoline-3-carboxylate

생성물 1

HCID 70670709HCID 70670709, 화합물

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

Methyl 6-bromoquinoline-3-carboxylate (Int-1, 0.25 g, 0.94 mmol), aniline (94 μL, 1.0 mmol), palladium(II) acetate (21 mg, 0.094 mmol), 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphine) (43 mg, 0.070 mmol), and cesium carbonate (431 mg, 1.32 mmol) were combined in a microwave vial fitted with a stirbar. N,N-Dimethylformamide (5.5 mL) was added, the vial was capped and the contents heated in a microwave at 100° C. for 1 h. The vial was cooled to room temperature, opened and the contents poured into water. The mixture was extracted three times with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (hexanes to 70/30 hexanes/ethyl acetate gradient) to afford pure Int-34. LC-MS: (FA) ES+ 279; 1H NMR (400 MHz, d6-DMSO) δ ppm 9.02 (d, J=2.1 Hz, 1 H), 8.79-8.74 (m, 2H), 7.94 (d, J=9.0 Hz, 1H), 7.67 (d, J=2.5 Hz, 1H), 7.62 (dd, J=9.1, 2.6 Hz, 1 H), 7.35-7.29 (m, 2H), 7.29-7.25 (m, 2H), 6.96 (tt, J=7.4, 7.4, 1.3, 1.3 Hz, 1H), 3.92 (s, 3H).

후처리

  1. customvial fitted with a stirbar
  2. customthe vial was capped
  3. temperatureThe vial was cooled to room temperature
  4. extractionThe mixture was extracted three times with ethyl acetate
  5. washThe extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude residue was purified by silica gel chromatography (hexanes to 70/30 hexanes/ethyl acetate gradient)
  10. customto afford pure Int-34

출처 및 근거

ORD 기록
ord-49aa6f830a7a42d3861e5a344ae28019
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513421B2

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