1,2-Dichloroethane → ethyl 6-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate

HRID 2410656Notes

Reaction equation

HRID 2410656 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([C:15](O)=[O:16])[CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:6][C:5]2=1.C(Cl)CCl.O.O[N:29]1C2C=CC=CC=2N=N1.[OH-].[NH4+]>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([C:15](=[O:16])[NH2:29])[CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:6][C:5]2=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 27960291-Hydroxybenzotriazole hydrateHCID 666044176-bromo-3-(ethoxycarbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid

Product 1

HCID 66605138ethyl 6-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a light suspension of 6-bromo-3-(ethoxycarbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid (2.12 g, 5.79 mmol), EDC (1.332 g, 6.95 mmol), and 1-hydroxybenzotriazole hydrate (1.064 g, 6.95 mmol) in THF/CH2Cl2 (5/1) (100 mL) was added ammonium hydroxide (1.353 mL, 34.7 mmol) and it turned into a thick light yellow suspension and it was stirred at rt overnight. The reaction was concentrated and the residue was dissolved in water/ethyl acetate. The organic phase was separated and washed with brine, dried over Na2SO4, filtered, concentrated to afford the crude product as a light yellow solid, which was washed with a small amount of ether and air-dried. The crude ethyl 6-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate was used as such in the next reaction.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in water/ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-59692cc74aca41b195eb7a55945689b0
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

Loading…