Cesium fluoride → (3-Fluoro-4'-methanesulfonyl-biphenyl-4-yl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

HRID 1867802ノート

反応式

HRID 1867802 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:9])=[C:4]([F:21])[CH:3]=1.[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)(=[O:25])=[O:24].[F-].[Cs+]>C(#N)C>[F:21][C:4]1[CH:3]=[C:2]([C:29]2[CH:30]=[CH:31][C:26]([S:23]([CH3:22])(=[O:25])=[O:24])=[CH:27][CH:28]=2)[CH:7]=[CH:6][C:5]=1[C:8]([N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:9]

参加物

5

反応物 3

HCID 25953Cesium fluorideHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 11965125(4-Bromo-2-fluoro-phenyl)-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

生成物 1

HCID 57980138(3-Fluoro-4'-methanesulfonyl-biphenyl-4-yl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Procedure EE: In a microwave reactor vessel, add (4-bromo-2-fluoro-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-yl)methanone (1.0 mmol), 4-methanesulfonylphenyl boronic acid (2.5 mmol), dichloropalladium di-triphenylphosphine (0.2 mmol), cesium fluoride (9.0 mmol) and acetonitrile (0.20M) and run in a CEM microwave reactor for 10 minutes at 120° C. with 75W power and cooling on. After this time, wash the reaction with water while extracting with 10% isopropanol/dichloromethane. Dry the organic layer with sodium sulfate, filter and concentrate in vacuo. Purify the title compound via radial chromatography eluting with 2M ammonia in methanol and dichloromethane. MS (m/e): 431.2 (M+1)

後処理

  1. temperaturecooling on
  2. washAfter this time, wash
  3. customthe reaction with water
  4. extractionwhile extracting with 10% isopropanol/dichloromethane
  5. dry with materialDry the organic layer with sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify the title compound via radial chromatography
  9. washeluting with 2M ammonia in methanol and dichloromethane

出典と根拠

ORDレコード
ord-d859029478ef4950ae6ef5546697b465
出典データセット
uspto-grants-2009_12
特許番号
US07632857B2

反応ノート

読み込み中…