2-Propynoic acid, 3-(4-fluorophenyl)-, methyl ester → HCID 17962385, compound

HRID 1374698Notes

Reaction equation

HRID 1374698 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:27][N+:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[CH:29]=1.N1(C2CCCCCCCCCC2)CCCN=CCCCCC1>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:33]3[CH:32]=[CH:31][C:30]([CH3:34])=[CH:29][N:28]3[N:27]=2)=[CH:6][CH:7]=1.[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:29]3[C:30]([CH3:34])=[CH:31][CH:32]=[CH:33][N:28]3[N:27]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 111268212-Propynoic acid, 3-(4-fluorophenyl)-, methyl esterHCID 1201314755899-02-0HCID 1296629601,8-Diazabicycloundec-7ene

Product 2

HCID 17962385HCID 17962385, compoundHCID 17962411HCID 17962411, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of methyl 3-(4-fluorophenyl)propiolate (Example 1 b) and 1-amino-3-methylpyridinium 2,4,6-trimethylbenzenesulfonate in dry acetonitrile was added, dropwise over 10 min, a solution of 1,8-diazabicycloundec-7-ene in dry acetonitrile. The mixture was allowed to stir at room temperature for about 18 h. The solvent was evaporated under reduced pressure and the residue was partitioned between water and ethyl acetate and the organic phase separated. The aqueous was extracted with ethyl acetate and the combined organic extracts are dried (MgSO4), and the solvent removed under vacuum. The residue was purified by chromatography on silica gel using 10:1 hexanes:ethyl acetate as eluent to give the title compound and also methyl 2-(4-fluorophenyl)-4-methyl-pyrazolo[1,5-a]pyridine-3-carboxylate.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. customthe organic phase separated
  4. extractionThe aqueous was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts are dried (MgSO4)
  6. customthe solvent removed under vacuum
  7. customThe residue was purified by chromatography on silica gel using 10:1 hexanes

Sources & evidence

ORD record
ord-ecfd89fd21ef4921ab3599df01c624a2
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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