Ammonia → 5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxamide

HRID 387255Notes

Reaction equation

HRID 387255 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11](O)=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:18][CH2:17][S:16](=[O:20])(=[O:19])[CH2:15]1.C1C=CC2N(O)N=[N:27]C=2C=1.CCN=C=NCCCN(C)C.Cl.N.CO>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:27])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:18][CH2:17][S:16](=[O:20])(=[O:19])[CH2:15]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 887MethanolHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 593327155-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxylic acid

Product 1

HCID 593325635-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxamideYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxylic acid (36 mg, 0.1 mmol) in DCM (5 mL) was added HOBt (16 mg, 0.12 mmol), and EDC.HCl (23 mg, 0.12 mmol) and 2 M NH3 in methanol (0.2 mL, 0.4 mmol). The mixture was kept overnight at RT. The mixture was concentrated, and EtOAc and aq. NaHCO3 were added. The aqueous layer was extracted with ethyl acetate once. The combined organic layers were dried (MgSO4) and concentrated to give 36 mg of the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. additionEtOAc and aq. NaHCO3 were added
  3. extractionThe aqueous layer was extracted with ethyl acetate once
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-88f5bc578d7542f6ab1140d99eb77999
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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