Sodium Iodide → HCID 58281264, compound

HRID 552318Notes

Reaction equation

HRID 552318 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([N:10]2[C:14]3=[N:15][C:16]([CH3:29])=[CH:17][C:18]([N:19]4[CH2:24][CH2:23][CH:22]([CH2:25][C:26]([OH:28])=[O:27])[CH2:21][CH2:20]4)=[C:13]3[C:12]([CH3:30])=[CH:11]2)=[C:5]([CH3:31])[CH:4]=1.[C:32](=[O:44])([O:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[O:33][CH:34](Cl)[CH3:35].C(=O)([O-])[O-].[K+].[K+].[Na+].[I-]>CN(C=O)C.O>[CH:38]1([O:37][C:32]([O:33][CH:34]([O:27][C:26](=[O:28])[CH2:25][CH:22]2[CH2:21][CH2:20][N:19]([C:18]3[CH:17]=[C:16]([CH3:29])[N:15]=[C:14]4[N:10]([C:6]5[C:7]([CH3:9])=[CH:8][C:3]([Br:2])=[CH:4][C:5]=5[CH3:31])[CH:11]=[C:12]([CH3:30])[C:13]=34)[CH2:24][CH2:23]2)[CH3:35])=[O:44])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 112295291-Chloroethyl Cyclohexyl CarbonateHCID 67152535HCID 67152535, compound

Product 1

HCID 58281264HCID 58281264, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of {1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetic acid hydrochloride (300 mg), 1-chloroethyl cyclohexyl carbonate (293 mg), potassium carbonate (196 mg) and NaI (213 mg) in DMF (3 mL) was heated at 60° C. for 3 hours. After cooling to room temperature, water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and concentrated under reduced pressure. The residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=4/1) to obtain the title compound (225 mg) as a colorless oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=4/1)

Sources & evidence

ORD record
ord-659fd88321374b7ba7e3d967670a7539
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

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