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

HRID 1690702

Reaction equation

HRID 1690702 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-1e8c2994e86a498d92cf684018961c13
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Linked notes

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