Sodium Bicarbonate → 1-[3-(4-(5-fluoro-3-indolyl)-1,2,3,6-tetrahydro-1-pyridyl)propyl]-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide

HRID 654101Notes

Reaction equation

HRID 654101 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:15]2=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14]2)[CH2:10][CH2:9][CH2:8][N:7]3[S:6]1(=[O:18])=[O:17].[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[C:29]1[CH2:30][CH2:31][NH:32][CH2:33][CH:34]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1>[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[C:29]1[CH2:30][CH2:31][N:32]([CH2:2][CH2:3][CH2:4][N:5]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=[CH:14]3)[CH2:10][CH2:9][CH2:8][N:7]4[S:6]2(=[O:18])=[O:17])[CH2:33][CH:34]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 113449595-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 198884501-(3-chloropropyl)-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide

Product 1

HCID 198884641-[3-(4-(5-fluoro-3-indolyl)-1,2,3,6-tetrahydro-1-pyridyl)propyl]-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxideYield 40.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The operation is as in Example 3, starting with 1-(3-chloropropyl)-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide (3.8 g), 4-(5-fluoro-3-indolyl)-1,2,3,6-tetrahydropyridine (2.9 g) and sodium bicarbonate (3.3 g) in a mixture of dimethylformamide (40 cc) and tetrahydrofuran (25 cc). The mixture is heated to boiling for 48 hours and is then cooled to a temperature close to 20° C. After purification by flash chromatography on a silica column, under a stream of argon at moderate pressure (0.5-1.5 bars) with ethyl acetate as eluent and recrystallization from boiling acetonitrile (200 cc), 1-[3-(4-(5-fluoro-3-indolyl)-1,2,3,6-tetrahydro-1-pyridyl)propyl]-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide (2.5 g) is obtained, melting at 178° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureis then cooled to a temperature
  3. customclose to 20° C
  4. customAfter purification by flash chromatography on a silica column
  5. customunder a stream of argon at moderate pressure (0.5-1.5 bars) with ethyl acetate as eluent and recrystallization

Sources & evidence

ORD record
ord-567a51a500d9415c8faa4d4cb24e9a59
Source dataset
uspto-grants-1992_07
Patent number
US05130313

Reaction notes

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