Diazobicycloundecane → HCID 22171173, compound

HRID 1822964Notes

Reaction equation

HRID 1822964 reaction equation
[Cl:1][C:2]1[C:6]2[C:7]([F:13])=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:5]=2[S:4][C:3]=1C(O)=O.[N+](=C1CCCCCCCCCC1C1CCCCCCCCCC1)=[N-]>CC(N(C)C)=O.C(OCC)C>[Cl:1][C:2]1[C:6]2[C:7]([F:13])=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:5]=2[S:4][CH:3]=1

Participants

5

Reactant 2

HCID 22171225DiazobicycloundecaneHCID 23568938HCID 23568938, compound

Product 1

HCID 22171173HCID 22171173, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 3-chloro-4-fluoro-7-methoxy-1-benzothiophene-2-carboxylic acid (1.09 g, 4.19 mmol) and diazobicycloundecane (DBU) (2 mL) in dimethylacetamide (15 mL) was heated in a sealed vessel in a microwave (300 W, 100%) for 1 h. After cooling to room temperature the mixture was diluted with diethyl ether (100 mL) and washed with brine (2×100 mL). The organic phase was dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography eluting silica gel with hexane:diethyl ether [10:1] to yield a white solid (520 mg, 57%); δH (300 MHz, CDCl3) 7.24 (1H, s, Ar), 7.05–6.92 (1H, m, Ar), 6.70–6.60 (1H, dd, Ar), 3.96 (3H, s, OCH3).

Workup

  1. temperaturewas heated in a sealed vessel in a microwave (300 W, 100%) for 1 h
  2. washwashed with brine (2×100 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting silica gel with hexane

Sources & evidence

ORD record
ord-8489a80c3fc5472ea3971e46e94f267d
Source dataset
uspto-grants-2006_05
Patent number
US07037932B2

Reaction notes

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