Cesium carbonate → HCID 59596015、化合物

HRID 2264190ノート

反応式

HRID 2264190 の反応式
Br[C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]([NH2:13])=[N:6][C:7]=1[C:8]1[O:9][CH:10]=[CH:11][N:12]=1.CC1(C)C(C)(C)OB([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[N+:14]([C:4]1[CH:3]=[C:2]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[C:7]([C:8]2[O:9][CH:10]=[CH:11][N:12]=2)=[N:6][C:5]=1[NH2:13])([O-:16])=[O:15]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 59595965HCID 59595965、化合物

生成物 1

HCID 59596015HCID 59596015、化合物収率 65%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
95 °C

実験手順

An oven-dried resealable Schlenk tube was charged with 5-bromo-3-nitro-6-(1,3-oxazol-2-yl)pyridin-2-amine (0.141 g, 0.49 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.203 g, 0.99 mmol), dioxane (5 mL) and a 2M aqueous solution of cesium carbonate (0.74 mL, 1.48 mmol). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex [PdCl2dppf.DCM] (0.024 g, 0.03 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was sealed and the mixture was stirred and heated in an oil bath to 95° C. After 20 hours, the mixture was cooled and partitioned between 2M aqueous hydrochloric acid and ethyl acetate. The aqueous phase was filtered through Celite® and the pH was adjusted to 5-6 with solid sodium hydroxide. The suspension was cooled in an ice bath and the precipitate was filtered, washed with water and dried to give the title compound (0.090 g, 65%) as a yellow solid.

後処理

  1. additionwas added
  2. customAfter three new cycles of evacuation-backfilling with argon, the Schlenk tube was sealed
  3. temperaturethe mixture was cooled
  4. custompartitioned between 2M aqueous hydrochloric acid and ethyl acetate
  5. filtrationThe aqueous phase was filtered through Celite®
  6. temperatureThe suspension was cooled in an ice bath
  7. filtrationthe precipitate was filtered
  8. washwashed with water
  9. customdried

出典と根拠

ORDレコード
ord-30b6633b8eca4e4f879285080c7d4df1
出典データセット
uspto-grants-2010_12
特許番号
US07855202B2

反応ノート

読み込み中…