Water → HCID 86599885, 화합물

HRID 16174

반응식

HRID 16174 반응식
Br[C:2]1[C:12]2[N:11]3[CH2:13][CH2:14][CH2:15][C@@H:16]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[C@H:10]3[C:9]3[CH:24]=[CH:25][CH:26]=[CH:27][C:8]=3[O:7][C:6]=2[CH:5]=[C:4]([F:28])[CH:3]=1.[Cl-].[CH3:30][Zn+].O>C1COCC1.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].Cl[Pd]Cl>[F:22][C:19]([F:21])([F:20])[C:18]([NH:17][C@H:16]1[C@@H:10]2[N:11]([C:12]3[C:2]([CH3:30])=[CH:3][C:4]([F:28])=[CH:5][C:6]=3[O:7][C:8]3[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=32)[CH2:13][CH2:14][CH2:15]1)=[O:23]

참가 물질

6

반응물 3

HCID 962WaterHCID 86599886HCID 86599886, 화합물HCID 178477797HCID 178477797, 화합물2회

생성물 1

HCID 86599885HCID 86599885, 화합물

시약·촉매·용매 2

HCID 131728027Ferrocene palladium dichloride촉매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a solution of trans-N-(6-bromo-8-fluoro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (300 mg, 0.65 mmol) in THF (7 mL) was added ferrocene PdCl2 (10 mg, 14 mmol) and the reaction mixture was stirred for 10 min. Methylzinc chloride (0.81 mL) was added dropwise whereafter the reaction mixture was heated to 60° C. After 3 h ferrocene PdCl2 (20 mg, 28 μmol) and methylzinc chloride (0.3 mL) were added and the reaction mixture was heated at 80° C. for another hour. Water was added at room temperature, and the reaction mixture was extracted with ether and water. The ether solution was washed with brine, dried (Na2SO4) and the volatiles were removed under reduced pressure. After purification by HPLC the title compound was obtained (108 mg, 39%). Data: 1H-NMR (400 MHz, CDCl3) 1.56-1.72 (m, 2H), 1.79-1.93 (m, 2H), 2.37 (s, 3H), 2.79-2.86 (m, 1H), 3.44-3.52 (td, J=12.0, J=3.0, 1H), 4.27-4.29 (d, J=2.5, 1H), 4.85-4.91 (m, 1H), 6.70-7.32 (6 ArH), 7.63-7.70 (br, 1H). (m/z)=395 (M+H)+.

후처리

  1. temperaturethe reaction mixture was heated at 80° C. for another hour
  2. extractionthe reaction mixture was extracted with ether and water
  3. washThe ether solution was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe volatiles were removed under reduced pressure
  6. customAfter purification by HPLC the title compound
  7. customwas obtained (108 mg, 39%)

출처 및 근거

ORD 기록
ord-e17dd38f63e74f9e9e1613f0722afdd2
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737136B2

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