Potassium Carbonate → 6-chloro-5-(3-methoxyphenyl)-1H-indole-3-carbaldehyde

HRID 1054643Notes

Reaction equation

HRID 1054643 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[CH:12]=[O:13].[CH3:14][O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.CN(C=O)C.O>[Cl:11][C:10]1[CH:9]=[C:8]2[C:4]([C:5]([CH:12]=[O:13])=[CH:6][NH:7]2)=[CH:3][C:2]=1[C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([O:15][CH3:14])[CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 866985665-bromo-6-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 866986466-chloro-5-(3-methoxyphenyl)-1H-indole-3-carbaldehydeYield 52.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 217120691,4-dioxane N,N-dimethylformamideSolvent

Procedure

To a solution of 5-bromo-6-chloro-1H-indole-3-carbaldehyde (300 mg, 2 mmol) in dioxane/DMF=1/1 (4 mL) was added (3-methoxyphenyl)boronic acid (463 mg, 1.8 mmol), potassium carbonate (828 mg, 6 mmol) in water (1 mL), and Pd (dppf)Cl2 (50 mg) in a microwave vial. The sealed vial was irradiated in the microwave on a Biotage Smith Synthesizer at 110° C. for 30 min, TLC (petroleum ether/ethyl acetate=1:1) showed the reaction was complete. The solvent was removed in vacuo and the mixture was partitioned between ethyl acetate and water. The combined organics were dried over sodium sulfate, concentrated in vacuo, and purified by combi-flash to give the title compound (270 mg, 47%) as a yellow solid

Workup

  1. customThe sealed vial was irradiated in the microwave on a Biotage Smith Synthesizer at 110° C. for 30 min
  2. customThe solvent was removed in vacuo
  3. customthe mixture was partitioned between ethyl acetate and water
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by combi-flash

Sources & evidence

ORD record
ord-67e60ab30dda4c8f995d611d2454726f
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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