Hydrochloric Acid → HCID 66777278, compound

HRID 2091186Notes

Reaction equation

HRID 2091186 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](N(OC)C)=[O:12])=[CH:5]2.[CH2:17]([Li])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl>O1CCCC1.CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:12])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:5]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 230033115-chloro-N-methoxy-N-methyl-1H-indole-2-carboxamideHCID 178506865HCID 178506865, compound2×

Product 1

HCID 66777278HCID 66777278, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Procedure

To a solution (100 mL) of 5-chloro-N-methoxy-N-methyl-1H-indole-2-carboxamide (9.14 g) synthesized above in tetrahydrofuran was added a 2.3M solution (50.0 mL) of hexyllithium in hexane at −78° C., and the mixture was stirred under nitrogen atmosphere for 1.5 hr. A 2.3M solution (38.3 mL) of hexyllithium in hexane was additionally added, and the mixture was stirred at −78° C. for 2 hr. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with hexane to give the title object compound (6.90 g, 68%) as a pale-yellow solid.

Workup

  1. stirringthe mixture was stirred at −78° C. for 2 hr
  2. customto quench
  3. customthe reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-a94ada14fc1d4ef3ab6cd1fe7c6209b8
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

Loading…