Cesium carbonate → 3-((3-(3-(4-fluorophenoxy)azetidin-1-yl)phenyl)amino)-N-methylbenzamide

HRID 522932노트

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HRID 522932 반응식
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:11][CH:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[NH2:20][C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([NH:26][CH3:27])=[O:25].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH:10]2[CH2:11][N:8]([C:4]3[CH:3]=[C:2]([NH:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24]([NH:26][CH3:27])=[O:25])[CH:7]=[CH:6][CH:5]=3)[CH2:9]2)=[CH:14][CH:15]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 6765263-Amino-N-methylbenzamideHCID 673548151-(3-Bromophenyl)-3-(4-fluorophenoxy)azetidine

생성물 1

HCID 533728563-((3-(3-(4-fluorophenoxy)azetidin-1-yl)phenyl)amino)-N-methylbenzamide수율 23.3%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

To a solution of 1-(3-bromophenyl)-3-(4-fluorophenoxy)azetidine (400 mg, 1.24 mmol) and 3-amino-N-methylbenzamide (187 mg, 1.24 mmol) in toluene (4 mL, 3 mmoL) was added cesium carbonate (180 mg, 1.86 mmol) and degassed for 15 min. Pd2(dba)3 (56 mg, 0.062 mmol) and BINAP (38 mg, 0.062 mmol) were added and the mixture was heated in the microwave for 30 min at 100° C. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×30 mL) and water (2×30 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure then purified by silica gel column chromatography to provide 3-((3-(3-(4-fluorophenoxy)azetidin-1-yl)phenyl)amino)-N-methylbenzamide (113 mg, 23%) as a solid. Observed mass (M+1): 393.1

후처리

  1. customdegassed for 15 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with EtOAc (2×30 mL) and water (2×30 mL)
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthen purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-a2f5a067739a4df9b9376169031e8e1c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334269B2

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