1,2-Dichloroethane → 6-bromo-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide

HRID 2410658Notes

Reaction equation

HRID 2410658 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([C:15](=[O:17])[NH2:16])[CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([C:18](O)=[O:19])[CH2:6][C:5]2=1.C(Cl)CCl.O.ON1C2C=CC=CC=2N=N1.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([C:15]([NH2:16])=[O:17])[CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([C:18]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)=[O:19])[CH2:6][C:5]2=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 27960291-Hydroxybenzotriazole hydrateHCID 666051346-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid

Product 1

HCID 666056046-bromo-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamideYield 92.2%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a solution of 6-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid (0.8 g, 2.135 mmol), EDC (0.491 g, 2.56 mmol), and 1-hydroxybenzotriazole hydrate (0.392 g, 2.56 mmol) in THF/CH2Cl2 (5/1) (30 mL) was added morpholine (0.4 mL, 4.27 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated and the solid was washed with ethyl acetate, and water. The organic layer was dried over Na2SO4 and concentrated to afford the crude product as a pale solid. The solid was washed with hexane-ethyl acetate to give 800 mg of pure 6-bromo-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide. MS (ESI) m/z 406 (M+H). 1H NMR (DMSO-d6) δ ppm 10.9 (s, 1H), 8.2 (bs, 1H), 7.81 (d, 1H), 7.75 (s, 1H), 3.92 (m, 4H), 3.77 (q, 2H, J=7.8 Hz), 2.52-2.81 (m, 7H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe solid was washed with ethyl acetate, and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customto afford the crude product as a pale solid
  6. washThe solid was washed with hexane-ethyl acetate

Sources & evidence

ORD record
ord-0226965f317b40fca89d12e35da36147
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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