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Cesium carbonate → 2-[(tert-Butyldimethylsilanyl)oxymethyl]phenyl-2-chloroimidazo[1,2-a]pyridine

HRID 2196442
ノート
印刷プレビュー

反応式

HRID 2196442 の反応式
Br[C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[Cl:17][C:18]1[N:19]=[C:20]2[CH:25]=[CH:24][C:23](B3OC(C)(C)C(C)(C)O3)=[CH:22][N:21]2[CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.O>[Si:6]([O:5][CH2:4][C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[C:35]1[N:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]2=[N:19][C:18]=1[Cl:17])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 13424900(2-Bromobenzyloxy)tert-butyldimethylsilaneHCID 442323732-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine

生成物 1

HCID 866520702-[(tert-Butyldimethylsilanyl)oxymethyl]phenyl-2-chloroimidazo[1,2-a]pyridine収率 46.7%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

450 mg of (2-bromobenzyloxy)-tert-butyldimethylsilane, 500 mg of 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine and 1.46 g of caesium carbonate are dissolved in 8 ml of tetrahydrofuran and 1 ml of water. The mixture is degassed with argon for 10 min, 110 mg of [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium are added and the mixture is heated at the reflux of the solvent for 16 hours. After cooling, the reaction mixture is hydrolysed with water, and the organic phase, which has been extracted with dichloromethane, is separated, dried and concentrated under reduced pressure. The oil obtained is purified by silica gel chromatography, elution being carried out with a heptane/ethyl acetate mixture. 260 mg of compound are obtained.

後処理

  1. customThe mixture is degassed with argon for 10 min
  2. addition110 mg of [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium are added
  3. temperaturethe mixture is heated at the
  4. temperaturereflux of the solvent for 16 hours
  5. temperatureAfter cooling
  6. extractionthe organic phase, which has been extracted with dichloromethane
  7. customis separated
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customThe oil obtained
  11. customis purified by silica gel chromatography, elution

出典と根拠

ORDレコード
ord-d9717c96f6fc459b91c5f9e7127a7d55
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08338451B2

反応ノート

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