Sodium Carbonate → 3,4-dihydro-8-fluoro-1-{2-[4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydro-1-pyridyl]-1-ethyl}-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide

HRID 583069Notes

Reaction equation

HRID 583069 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:9]2[C:10]([F:14])=[CH:11][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.[Na+].[Na+]>O>[F:14][C:10]1[C:9]2[N:4]([CH2:3][CH2:2][N:33]3[CH2:34][CH2:35][C:30]([C:25]4[C:24]5[C:28](=[CH:29][C:21]([F:20])=[CH:22][CH:23]=5)[NH:27][CH:26]=4)=[CH:31][CH2:32]3)[S:5](=[O:19])(=[O:18])[N:6]([CH:15]([CH3:17])[CH3:16])[CH2:7][C:8]=2[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 110530726-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 177771701-(2-chloroethyl)-3,4-dihydro-8-fluoro-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide

Product 1

HCID 158604033,4-dihydro-8-fluoro-1-{2-[4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydro-1-pyridyl]-1-ethyl}-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 1-(2-chloroethyl)-3,4-dihydro-8-fluoro-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide (1.35 g), 4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydropyridine (31.45 g, 6.7 mmol) and Na2CO3 (3.6 g, 34.6 mmol) in water (8 ml) was heated at 100° C. under argon atmosphere for 30 hours. After cooling to room temperature the product was extracted with dichloromethane. The organic phase was dried over Na2SO4 and evaporated to dryness. The crude mixture was purified by flash chromatography using as eluent CH2Cl2 /MeOH (97:3) yielding 3,4-dihydro-8-fluoro-1-{2-[4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydro-1-pyridyl]-1-ethyl}-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide as a pale brown solid.

Workup

  1. temperatureAfter cooling to room temperature the product
  2. extractionwas extracted with dichloromethane
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated to dryness
  5. customThe crude mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-e1ea9aa337ba4fd5ae58adce6845a6bc
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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