Cesium carbonate → HCID 59596015, 화합물

HRID 2264190노트

반응식

HRID 2264190 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

HCID 59596015HCID 59596015, 화합물수율 65%

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
95 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-30b6633b8eca4e4f879285080c7d4df1
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855202B2

반응 노트

불러오는 중…