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

HRID 1690702

反応式

HRID 1690702 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 576184806-Nitro-5-vinyl-indan-1-one収率 79%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 21881883Oxolane--water (1/1)溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1e8c2994e86a498d92cf684018961c13
出典データセット
uspto-grants-2012_04
特許番号
US08153671B2

関連ノート

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