Potassium Carbonate → 6-chloro-5-[4-(5-oxomorpholin-2-yl)phenyl]-1H-indole-3-carbaldehyde

HRID 338414Notes

Reaction equation

HRID 338414 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1B1OCC(C)(C)CO1.[C:19](=O)([O-])[O-:20].[K+].[K+].Br[C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[CH2:37][NH:36][C:35](=[O:38])[CH2:34][O:33]2)=[CH:28][CH:27]=1>CN(C=O)C.O1CCOCC1.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]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:19]=[O:20])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[O:33][CH2:34][C:35](=[O:38])[NH:36][CH2:37]2)=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 778147346-(4-Bromophenyl)morpholin-3-oneHCID 866987336-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole

Product 1

HCID 866987506-chloro-5-[4-(5-oxomorpholin-2-yl)phenyl]-1H-indole-3-carbaldehydeYield 75%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 217120691,4-dioxane N,N-dimethylformamideSolvent

Procedure

The mixture of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (150 mg, 0.57 mmol) and N,N-dimethylformiminium chloride (217 mg, 1.70 mmol) in DMF/dioxane (6 mL, 1:5) was stirred at room temperature for 20 minutes. Then 2.0M potassium carbonate (3 mL), 6-(4-bromophenyl)morpholin-3-one (146 mg, 0.57 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (41 mg, 0.057 mmol) was added to the mixture. The reaction mixture was purged with nitrogen for 3 minutes, heated to 90° C. and stirred for 30 minutes. The reaction mixture was extracted with ethyl acetate (10 mL×3). The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the title compound (150 mg, 75% yield) as a brown solid that was brought forward without further purification.

Workup

  1. customThe reaction mixture was purged with nitrogen for 3 minutes
  2. temperatureheated to 90° C.
  3. stirringstirred for 30 minutes
  4. extractionThe reaction mixture was extracted with ethyl acetate (10 mL×3)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e737226907ff475abb04f3d56fc8965c
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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