Potassium Carbonate → tert-butyl 2-(5-chloro-3-formyl-1H-indol-1-yl)acetate

HRID 1527210Notes

Reaction equation

HRID 1527210 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]=[O:12].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CCOC(C)=O.O>[C:24]([O:23][C:21](=[O:22])[CH2:20][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[C:5]([CH:11]=[O:12])=[CH:6]1)([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 27953745-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 86673814tert-butyl 2-(5-chloro-3-formyl-1H-indol-1-yl)acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5-chloro-1H-indole-3-carbaldehyde [827-01-0] (500 mg, 2.78 mmol) and K2CO3 (885 mg, 6.40 mmol) in (14 mL) was added tert-butyl 2-bromoacetate (0.576 mL, 3.90 mmol) dropwise at RT. The resulting mixture was then heated to reflux for 18 h. After cooling to RT, the mixture was diluted with EtOAc and water. The organic layer was separated, subsequently washed with water (1×) and brine (1×), dried (Phase separator) and concentrated in vacuo to give the crude title compound. MS (LC/MS): 294 [M+H]+; tR (HPLC conditions b): 5.45 min. The product was used in the next reaction step without further purification.

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureto reflux for 18 h
  3. customThe organic layer was separated
  4. washsubsequently washed with water (1×) and brine (1×)
  5. customdried (Phase separator)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8cca49e54371453e9912362d0f1f746b
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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