Sodium Carbonate → 1-(propan-2-yl)-5-(2,3,4-trifluorophenyl)-1H-indole-3-carbaldehyde

HRID 402819Notes

Reaction equation

HRID 402819 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH:17]([CH3:19])[CH3:18])[CH:12]=[C:11]2[CH:20]=[O:21].[F:22][C:23]1[C:28]([F:29])=[C:27]([F:30])[CH:26]=[CH:25][C:24]=1B(O)O>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:18][CH:17]([N:13]1[C:14]2[C:10](=[CH:9][C:8]([C:26]3[CH:25]=[CH:24][C:23]([F:22])=[C:28]([F:29])[C:27]=3[F:30])=[CH:16][CH:15]=2)[C:11]([CH:20]=[O:21])=[CH:12]1)[CH3:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27832802,3,4-Trifluorobenzeneboronic acidHCID 50503775-Bromo-1-(1-methylethyl)-1H-indole-3-carboxaldehyde

Product 1

HCID 866852731-(propan-2-yl)-5-(2,3,4-trifluorophenyl)-1H-indole-3-carbaldehydeYield 83.8%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Sodium carbonate (0.188 mL, 2M, 0.376 mmol) was added to a stirred room temperature solution of 5-bromo-1-(propan-2-yl)-1H-indole-3-carbaldehyde (50 mg, 0.188 mmol), 2,3,4-trifluorophenylboronic acid (66 mg, 0.376 mmol) and PdCl2(dppf) (13.7 mg, 0.019 mmol) in DMF (1.0 mL) and the reaction mixture was stirred at 80° C. for 12 hours. The reaction mixture was cooled to room temperature, partitioned between ethyl acetate (2×15 mL) and water (10 mL), washed with saturated sodium bicarbonate (10 mL), brine (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (50 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate (2×15 mL) and water (10 mL)
  3. washwashed with saturated sodium bicarbonate (10 mL), brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-910940917b6342969e7c05a6841a63c2
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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