Sodium Carbonate → 3,3-Dimethyl-1-{2-[4-(7-fluoroindol-3-yl)-1,2,5,6-tetrahydro-1-pyridyl]-1-ethyl}-1,3-dihydro-2H-indol-2-one

HRID 1276335Notes

Reaction equation

HRID 1276335 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH:12]=1.[CH3:17][C:18]1([CH3:35])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([CH2:27][CH2:28]OS(C)(=O)=O)[C:19]1=[O:34].C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:35][C:18]1([CH3:17])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([CH2:27][CH2:28][N:14]2[CH2:15][CH2:16][C:11]([C:7]3[C:6]4[C:10](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=4)[NH:9][CH:8]=3)=[CH:12][CH2:13]2)[C:19]1=[O:34]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 120834537-Fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 221161053,3-dimethyl-1-(2-methanesulfonyloxy-1-ethyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 98658883,3-Dimethyl-1-{2-[4-(7-fluoroindol-3-yl)-1,2,5,6-tetrahydro-1-pyridyl]-1-ethyl}-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(7-Fluoroindol-3-yl)-1,2,5,6-tetrahydropyridine (2.0 g, 9.26 mmols), 3,3-dimethyl-1-(2-methanesulfonyloxy-1-ethyl)-1,3-dihydro-2H-indol-2-one (2.623 g, 9.26 mmols), sodium carbonate (2.947 g,27.8 mmols),water (20 mls) combined and heated to 90 deg C. for 3 hours. Extracted into ethyl acetate (2×50 ml). Dried (MgSO4),filtered and concentrated in vacuo. The resultant solid was recrystallised from ethyl acetate and then converted to the hydrochloride salt (0.85 g).m.p 235-236 deg. C.

Workup

  1. temperatureheated to 90 deg C
  2. extractionExtracted into ethyl acetate (2×50 ml)
  3. concentrationDried (MgSO4),filtered and concentrated in vacuo
  4. customThe resultant solid was recrystallised from ethyl acetate
  5. customconverted to the hydrochloride salt (0.85 g).m.p 235-236 deg. C

Sources & evidence

ORD record
ord-79d85607ce6e4207bc0d17bcd9c36a07
Source dataset
uspto-grants-2000_12
Patent number
US06166040

Reaction notes

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