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Cesium carbonate → (S)-tert-butyl (1-(3-bromo-6-(3-hydroxy-3-methylazetidin-1-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

HRID 2170377
ノート
印刷プレビュー

反応式

HRID 2170377 の反応式
[Br:1][C:2]1[C:3]([C@@H:9]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)=[N:4][C:5](Br)=[CH:6][CH:7]=1.Cl.[CH3:28][C:29]1([OH:33])[CH2:32][NH:31][CH2:30]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[Br:1][C:2]1[C:3]([C@@H:9]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)=[N:4][C:5]([N:31]2[CH2:32][C:29]([OH:33])([CH3:28])[CH2:30]2)=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 115427813-methylazetidin-3-ol HydrochlorideHCID 90290190tert-Butyl (S)-(1-(3,6-dibromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

生成物 1

HCID 90290192(S)-tert-butyl (1-(3-bromo-6-(3-hydroxy-3-methylazetidin-1-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

試薬・触媒・溶媒

2
HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
150 °C

実験手順

(S)-tert-butyl (1-(3,6-dibromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate (150 mg, 0.3 mmol), 3-methylazetidin-3-ol hydrochloride (75 mg, 0.6 mmol) was combined with cesium carbonate (397 mg, 1.2 mmol), palladium diacetate (10 mg, 0.015 mmol) and 2,2′-bis-(diphenylphosphino)-1,1′-binaphthyl (19 mg, 0.03 mmol) in 2 mL of toluene. The system was degassed and purged with argon and heated to 150° C. heating bath for 1 hour, the reaction mixture was cooled and diluted with ethyl acetate. The organic layer was washed with water and brine, and then dried over sodium sulfate. The crude was purified by flash chromatography eluting with EtOAc/hexanes to provided the title compound. MS (m/z) 499.72 [M+H]+.

後処理

  1. customThe system was degassed
  2. custompurged with argon
  3. temperatureheating bath for 1 hour
  4. temperaturethe reaction mixture was cooled
  5. additiondiluted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customThe crude was purified by flash chromatography
  9. washeluting with EtOAc/hexanes

出典と根拠

ORDレコード
ord-63abe716d610486b9e3aa07ef2dc712c
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09050344B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート