Water → 2-fluorodibenzo[b,f][1,4]oxazepin-11(10H)-one

HRID 1946572노트

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HRID 1946572 반응식
[NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:6]=1[C:7](OC)=[O:8].C[Al](C)C.C1(C)C=CC=CC=1.O>C(Cl)Cl>[F:15][C:12]1[CH:13]=[CH:14][C:5]2[O:4][C:3]3[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=3[NH:1][C:7](=[O:8])[C:6]=2[CH:11]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 1140TolueneHCID 16682925TrimethylaluminumHCID 59783706Methyl 2-(2-aminophenoxy)-5-fluorobenzoate

생성물 1

HCID 122595332-fluorodibenzo[b,f][1,4]oxazepin-11(10H)-one수율 73%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Title compound 19 (802 mg, 3.07 mmol) was dissolved in DCM (10 mL) and the mixture was cooled to 0° C. Trimethylaluminum 2M in toluene (1.8 mL, 3.69 mmol) was added dropwise and the reaction mixture was allowed to warm to room temperature. The mixture was then heated to 45° C. for 45 h. The mixture was cooled to room temperature for the slow addition of water. The solution was extracted with ethyl acetate then washed twice with HCl (10%), water and saturated solution of bicarbonate. The organic layer was then dried over sodium sulfate and concentrated in vacuo until the product precipitated. The solid was filtered and dried to afford title compound 20 (511 mg, 73%) as a white solid. LRMS (ESI): (calc) 229.05 (found) 230.1 (MS)+.

후처리

  1. temperatureto warm to room temperature
  2. temperatureThe mixture was then heated to 45° C. for 45 h
  3. extractionThe solution was extracted with ethyl acetate
  4. washthen washed twice with HCl (10%), water and saturated solution of bicarbonate
  5. dry with materialThe organic layer was then dried over sodium sulfate
  6. concentrationconcentrated in vacuo until the product
  7. customprecipitated
  8. filtrationThe solid was filtered
  9. customdried

출처 및 근거

ORD 기록
ord-423e55a7e9144145abe17e4c9797a7d5
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399452B2

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