Sodium Carbonate → 6-Nitro-5-vinyl-indan-1-one

HRID 1690702

반응식

HRID 1690702 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:7](=[O:14])[CH2:6][CH2:5]2.[CH2:15](OB(C=C)OCCCC)[CH2:16]CC.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.O>[N+:11]([C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][C:7]2=[O:14])=[CH:3][C:2]=1[CH:15]=[CH2:16])([O-:13])=[O:12]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 236543Dibutyl Vinylboronate (stabilized with Phenothiazine)HCID 534851495-bromo-6-nitro-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 576184806-Nitro-5-vinyl-indan-1-one수율 79%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 21881883Oxolane--water (1/1)용매

실험 절차

A solution of 5-bromo-6-nitro-indan-1-one (58 mg, 0.23 mmol), (J. Med. Chem., 2003, 46, 399-408), vinylboronic acid dibutyl ester (74 μL, 0.34 mmol), Pd(PPh3)2Cl2 (7.8 mg, 0.0011 mmol), and Na2CO3 (167 mg, 1.57 mmol) in 4:1 THF/H2O (1.4 mL/360 μL) was heated to 80° C. overnight. The crude reaction was filtered over Celite and extracted with EtOAC. The organic phase was dried (MgSO4), filtered, and concentrated. The crude material was chromatographed (SiO2) to afford 36 mg (79%) of 6-Nitro-5-vinyl-indan-1-one; LC/MS calculated for [M+H]+ C11H9NO2: 204.1, found: 204.1.

후처리

  1. customThe crude reaction
  2. filtrationwas filtered over Celite
  3. extractionextracted with EtOAC
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was chromatographed (SiO2)

출처 및 근거

ORD 기록
ord-1e8c2994e86a498d92cf684018961c13
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153671B2

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