4-Aminophenol → 4-(7-Methoxy-1,5-naphthyridin-4-yloxy)benzenamine

HRID 503524노트

반응식

HRID 503524 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:16]1[CH:17]=[CH:18][N:19]=[C:20]2[C:25]=1[N:24]=[CH:23][C:22]([O:26][CH3:27])=[CH:21]2.O>CN(C=O)C>[CH3:27][O:26][C:22]1[CH:21]=[C:20]2[C:25]([C:16]([O:8][C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=3)=[CH:17][CH:18]=[N:19]2)=[N:24][CH:23]=1

참가 물질

6

반응물 4

HCID 4034-AminophenolHCID 962WaterHCID 10796Cesium carbonateHCID 594273408-Chloro-3-methoxy-1,5-naphthyridine

생성물 1

HCID 441851064-(7-Methoxy-1,5-naphthyridin-4-yloxy)benzenamine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Five 20 mL microwave vials were each charged with 4-aminophenol (0.700 mg, 33 mmol) and 3 equivalents of cesium carbonate in 6.0 ml of DMF. The mixture was stirred at RT for 10 minutes. Following addition of 8-chloro-3-methoxy-1,5-naphthyridine (1 g, 26 mmol), the reaction vessels were capped and irradiated at 150° C. for 15 min in the microwave, at which time the reaction was determined complete by LCMS. The mixture was allowed to cool to ambient temperature and material from the five vessels was combined. A deep brown solid crashed out with addition of water. Filtered solids, washed with water and dried overnight in the vacuum oven to afford 4-(7-methoxy-1,5-naphthyridin-4-yloxy)benzenamine as a brown solid.

후처리

  1. customthe reaction vessels
  2. customwere capped
  3. customirradiated at 150° C. for 15 min in the microwave, at which time the reaction
  4. temperatureto cool to ambient temperature
  5. filtrationFiltered solids
  6. washwashed with water
  7. customdried overnight in the vacuum oven

출처 및 근거

ORD 기록
ord-cd70aa3c42fc41999055d438f1182d14
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776857B2

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