Potassium Carbonate → Methyl[6-chloro-2-(4-ethylpyridine-2-carbonyl)-1H-indol-3-yl]acetate

HRID 396454Notes

Reaction equation

HRID 396454 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5](/[CH:6]=[CH:7]/[C:8]([O:10][CH3:11])=[O:9])=[C:4]([NH:14]S(C2C=CC=CC=2)(=O)=O)[CH:3]=1.Br[CH2:25][C:26]([C:28]1[CH:33]=[C:32]([CH2:34][CH3:35])[CH:31]=[CH:30][N:29]=1)=[O:27].C(=O)([O-])[O-].[K+].[K+].N12CCCN=C1CCCCC2>CC(C)=O>[CH3:11][O:10][C:8](=[O:9])[CH2:7][C:6]1[C:5]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:13][CH:12]=2)[NH:14][C:25]=1[C:26]([C:28]1[CH:33]=[C:32]([CH2:34][CH3:35])[CH:31]=[CH:30][N:29]=1)=[O:27]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11371593Methyl trans-4-chloro-2-(phenylsulfonylamino)cinnamateHCID 230032632-Bromoacetyl-4-ethylpyridine

Product 1

HCID 23003267Methyl[6-chloro-2-(4-ethylpyridine-2-carbonyl)-1H-indol-3-yl]acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl trans-4-chloro-2-(phenylsulfonylamino)cinnamate (step 1 of Example 8, Method A, 700 mg, 1.99 mmol), 2-bromoacetyl-4-ethylpyridine* (545 mg, 2.39 mmol), potassium carbonate (1.37 g, 13.9 mmol) and acetone (20 ml) was stirred at room temperature. After stirring for 3 h, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.6 ml, 3.98 mmol) was added. The resulting mixture was stirred for an additional 19 h and then concentrated. The residue was diluted with dichloromethane (200 ml) and washed with water (100 ml×2). The organic layer was dried (MgSO4) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate/hexane/dichloromethane (1:4:1) to give the title compound including impurity. The crude product was washed with ethyl acetate to give 297 mg (42%) of the title compound as yellow solids.

Workup

  1. stirringAfter stirring for 3 h
  2. stirringThe resulting mixture was stirred for an additional 19 h
  3. concentrationconcentrated
  4. additionThe residue was diluted with dichloromethane (200 ml)
  5. washwashed with water (100 ml×2)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography
  9. washeluting with ethyl acetate/hexane/dichloromethane (1:4:1)

Sources & evidence

ORD record
ord-4b2fdce2ea3449348dcf26e1079c9620
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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