Water → HCID 86599885、化合物

HRID 16174

反応式

HRID 16174 の反応式
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]

参加物

6

反応物 3

HCID 962WaterHCID 86599886HCID 86599886、化合物HCID 178477797HCID 178477797、化合物2 回

生成物 1

HCID 86599885HCID 86599885、化合物

試薬・触媒・溶媒 2

HCID 131728027Ferrocene palladium dichloride触媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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)+.

後処理

  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%)

出典と根拠

ORDレコード
ord-e17dd38f63e74f9e9e1613f0722afdd2
出典データセット
uspto-grants-2010_06
特許番号
US07737136B2

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