Diazobicycloundecane → HCID 22171173, compound

HRID 2220311Notes

Reaction equation

HRID 2220311 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 (300W, 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. washwashed with brine (2×100 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by flash chromatography
  5. washeluting silica gel with hexane

Sources & evidence

ORD record
ord-4026e45921a94a1c9bab8f87f77f3617
Source dataset
uspto-grants-2008_08
Patent number
US07417064B2

Reaction notes

Loading…