1,2-Dichloroethane → 5-bromo-1H-indole-7-carboxamide

HRID 1806199Notes

Reaction equation

HRID 1806199 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=O)[CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(Cl)CCl.C1C=CC2N(O)N=[N:24]C=2C=1.N>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:24])=[O:13])[CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 533992575-Bromo-1H-indole-7-carboxylic acid

Product 1

HCID 596006575-bromo-1H-indole-7-carboxamideYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-1H-indole-7-carboxylic acid (10.0 g, 42 mmol) in CH2Cl2 (100 mL) at room temperature, EDC (9.66 g, 50.4 mmol), HOBt (6.81 g, 50.4 mmol) and NH3 (2.0 M in MeOH, 84 mL, 168 mmol) were added. The reaction mixture was stirred at room temperature for 16 hours. The solvent was evaporated and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The water layer was extracted with ethyl acetate (100 mL×2) and the combined organic phase was dried over MgSO4 and concentrated to give the crude product (10 g, 98%). This crude product was used directly in the next step without further purification. LC/MS: m/z 240.0 (M+H), 1.95 min.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate (100 mL) and water (100 mL)
  3. extractionThe water layer was extracted with ethyl acetate (100 mL×2)
  4. dry with materialthe combined organic phase was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cb72a04f4c1a4f87a676df4e28eb8d49
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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