Potassium Carbonate → HCID 44214761, compound

HRID 583075Notes

Reaction equation

HRID 583075 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]=2[CH2:7][N:6]([CH:15]([CH3:17])[CH3:16])[S:5]1(=[O:19])=[O:18].[F:20][C:21]1[CH:29]=[C:28]2[C:24]([C:25]([C:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH:31]=3)=[CH:26][NH:27]2)=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>O>[F:20][C:21]1[CH:29]=[C:28]2[C:24]([C:25]([C:30]3[CH2:35][CH2:34][N:33]([CH2:2][CH2:3][N:4]4[C:9]5[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]=5[CH2:7][N:6]([CH:15]([CH3:17])[CH3:16])[S:5]4(=[O:19])=[O:18])[CH2:32][CH:31]=3)=[CH:26][NH:27]2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110530726-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 17777167HCID 17777167, compound

Product 1

HCID 44214761HCID 44214761, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a 25 ml two-necked flask equipped with a reflux condenser and in Argon atmosphere, were added 1-(2-chloroethyl)-3,4-dihydro-7-fluoro-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide(678 mg, 2.2 mmol), 4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydropyridine (523 mg, 242 mmol), anhydrous K2CO3 (1.09 g, 11 mmol) and 10 ml of deionised water. The mixture was vigorously stirred under Argon for 64 hours at 100° C., allowed to reach room temperature and extracted with EtOAc (3×25 ml). The combined organic extracts were dried (Na2SO4) and solvent removed at reduced pressure. The residue was purified by flash chromatography on silica gel (EtOAc:hexane 1:3) affording 3,4-dihydro-1-{2-[4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydro-1-pyridyl]-1-ethyl}-3-(1-methylethyl)-7-fluoro-1H-2,1,3-benzothiadiazine-2,2-dioxide as a pale yellow solid, m.p. 103-105°.

Workup

  1. customTo a 25 ml two-necked flask equipped with a reflux condenser and in Argon atmosphere
  2. customto reach room temperature
  3. extractionextracted with EtOAc (3×25 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4) and solvent
  5. customremoved at reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (EtOAc:hexane 1:3)

Sources & evidence

ORD record
ord-20734eaadad643b19d029d97a83b7f6a
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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