Hydrochloric Acid → 9-bromo-6-carbamoyl-5H-pyrido[4,3-b]indole-3-carboxylic acid

HRID 2361442Notes

Reaction equation

HRID 2361442 reaction equation
[Br:1][C:2]1[C:3]2[C:4]3[CH:16]=[N:15][C:14]([C:17]([O:19]CC)=[O:18])=[CH:13][C:5]=3[NH:6][C:7]=2[C:8]([C:11]#[N:12])=[CH:9][CH:10]=1.B1([O-])O[O:23]1.O.O.O.O.[Na+].Cl>C(O)C.O>[Br:1][C:2]1[C:3]2[C:4]3[CH:16]=[N:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][C:5]=3[NH:6][C:7]=2[C:8]([C:11](=[O:23])[NH2:12])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 67995622ethyl 9-bromo-6-cyano-5H-pyrido[4,3-b]indole-3-carboxylate

Product 1

HCID 679948609-bromo-6-carbamoyl-5H-pyrido[4,3-b]indole-3-carboxylic acidYield 79.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of crude ethyl 9-bromo-6-cyano-5H-pyrido[4,3-b]indole-3-carboxylate (0.78 g, 2.266 mmol) and sodium perborate tetrahydrate (1.395 g, 9.07 mmol) in ethanol-water (3:2, 99 mL) was heated at 100° C. for 3 h. The mixture was cooled to room temperature and the ethanol was removed under vacuum to give a suspension. The pH was adjusted to about 5-6 with 1 M aqueous HCl. The precipitate was collected by filtration, washed with water and air-dried to afford the desired product (0.60 g). The filtrate was concentrated under vacuum to provide additional desired product (70 mg, total of 88% yield). LCMS (M+H)+ m/z 334.0, 335.9.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe ethanol was removed under vacuum
  3. customto give a suspension
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-0af96d60ad194108864d4e6a3503bf99
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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