Sodium Bicarbonate → methyl 1-chloro-5H-pyrido[4,3-b]indole-4-carboxylate

HRID 1896516Notes

Reaction equation

HRID 1896516 reaction equation
[N:1]1([C:10]2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:13]=[C:12]([Cl:20])[CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2N=N1.C([O-])(O)=O.[Na+]>>[Cl:20][C:12]1[C:11]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[NH:1][C:10]=2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:13]=1

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 59198426Methyl 4-(1H-1,2,3-benzotriazol-1-yl)-6-chloronicotinate

Product 1

HCID 59198422methyl 1-chloro-5H-pyrido[4,3-b]indole-4-carboxylate

Conditions

Temperature
150 °C

Procedure

A suspension of methyl 4-(1H-1,2,3-benzotriazol-1-yl)-6-chloronicotinate in PPA (1 M) was heated in a preheated oil bath at 150° C. for a period of 10-15 min. The reaction mixture was cooled to room temperature, poured slowly and carefully into an aqueous solution containing NaHCO3 solid. The aqueous phase was extracted with EtOAc, washed with brine, and the organic phase was separated, dried over MgSO4 and filtered. After evaporation of the organic solvent, the residue was purified by flash chromatography (10-70% EtOAc in hexanes) to provide the title compound as a pale yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionpoured slowly and carefully into an aqueous solution
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washwashed with brine
  5. customthe organic phase was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customAfter evaporation of the organic solvent
  9. customthe residue was purified by flash chromatography (10-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-21adc88eca94477b967645fae5d47593
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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