Acetic Acid → HCID 178437998, compound

HRID 237405Notes

Reaction equation

HRID 237405 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=O)[CH:10]=2)[NH:5][N:4]=1)[CH3:2].[C:14](/[CH:16]=[C:17](\[O-:19])/[CH3:18])#[N:15].[Na+].C(O)(=O)C.N1CCCCC1>ClCCl>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](/[CH:12]=[C:16](/[C:17](=[O:19])[CH3:18])\[C:14]#[N:15])[CH:10]=2)[NH:5][N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 23687916sodium (1Z)-1-cyanoprop-1-en-2-olateHCID 178437999HCID 178437999, compound

Product 1

HCID 178437998HCID 178437998, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.50 g (2.87 mmol) 3-ethyl-1H-indazole-5-carbaldehyde (Example 8A), 0.33 g (3.16 mmol) sodium (1Z)-1-cyanoprop-1-en-2-olate, 0.21 ml (3.6 mmol) acetic acid and 0.028 ml (0.29 mmol) piperidine in dry dichloromethane (25 ml) containing 4 Å molecular sieve was stirred under reflux for 16 h. Upon cooling, a precipitate was formed which was collected by filtration and washed with saturated aqueous sodium bicarbonate solution and water. The solid was dissolved in ethanol, and the molecular sieve was filtered off. The filtrate was concentrated under reduced pressure, and the residue was treated with ethyl acetate and saturated aqueous sodium carbonate solution. The organic layer was washed with water, dried, and concentrated under reduced pressure to afford the title compound (0.60 g, 88% of th.) as a pale yellow solid which was used in subsequent steps without further purification.

Workup

  1. additioncontaining 4 Å molecular sieve
  2. temperatureunder reflux for 16 h
  3. temperatureUpon cooling
  4. customa precipitate was formed which
  5. filtrationwas collected by filtration
  6. washwashed with saturated aqueous sodium bicarbonate solution and water
  7. dissolutionThe solid was dissolved in ethanol
  8. filtrationthe molecular sieve was filtered off
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. additionthe residue was treated with ethyl acetate and saturated aqueous sodium carbonate solution
  11. washThe organic layer was washed with water
  12. customdried
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0cc1ed8f702240b39b333813066c93ac
Source dataset
uspto-grants-2014_02
Patent number
US08642595B2

Reaction notes

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