Cesium carbonate → 4-Methyl-3-(2'-oxospiro[cyclopentane-1,3'-indoline]-6'-yl)benzoic acid

HRID 1619126

반응식

HRID 1619126 반응식
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH2:15][CH2:14][CH2:13][CH2:12]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH3:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=1[C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH2:15][CH2:14][CH2:13][CH2:12]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 127170906'-Bromospiro[cyclopentane-1,3'-indolin]-2'-oneHCID 160860864-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

생성물 1

HCID 581704674-Methyl-3-(2'-oxospiro[cyclopentane-1,3'-indoline]-6'-yl)benzoic acid수율 81%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
105 °C

실험 절차

An oven-dried resealable Schlenk tube was charged with 6′-bromospiro[cyclopentane-1,3′-indolin]-2′-one (preparation 2, 0.650 g, 2.44 mmol), 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (WO200700565, 0.96 g, 3.66 mmol), 1,4-dioxane (25 mL) and a 2M aqueous cesium carbonate solution (3.7 mL, 7.4 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 (0.12 g, 0.15 mmol) was added. After three further cycles of evacuation-backfilling with argon, the Schlenk tube was sealed and the mixture was stirred and heated in an oil bath to 100-110° C. After 20 hours, the mixture was cooled and partitioned between water and ethyl acetate. The combined organic extract was dried (MgSO4) and evaporated in vacuo. Purification of the residue by flash chromatography (95:5 dichloromethane/methanol) gave the title compound (0.64 g, 81%) as a yellow solid.

후처리

  1. additionwas added
  2. customAfter three further cycles of evacuation-backfilling with argon, the Schlenk tube was sealed
  3. temperaturethe mixture was cooled
  4. custompartitioned between water and ethyl acetate
  5. extractionThe combined organic extract
  6. dry with materialwas dried (MgSO4)
  7. customevaporated in vacuo
  8. customPurification of the residue by flash chromatography (95:5 dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-1dbfcae98be14fcc9c4114d9a2eb90b4
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772288B2

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