Sodium Iodide → HCID 18332434, compound

HRID 2268786Notes

Reaction equation

HRID 2268786 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])=[CH:13][C:8]=2[CH2:7][N:6]([CH:19]([CH3:21])[CH3:20])[S:5]1(=[O:23])=[O:22].[F:24][C:25]1[CH:33]=[C:32]2[C:28]([C:29]([C:34]3[CH2:35][CH2:36][NH:37][CH2:38][CH:39]=3)=[CH:30][NH:31]2)=[CH:27][CH:26]=1.[I-].[Na+].C(=O)(O)[O-].[Na+]>O>[CH2:17]([S:14]([C:12]1[CH:11]=[CH:10][C:9]2[N:4]([CH2:3][CH2:2][N:37]3[CH2:38][CH:39]=[C:34]([C:29]4[C:28]5[C:32](=[CH:33][C:25]([F:24])=[CH:26][CH:27]=5)[NH:31][CH:30]=4)[CH2:35][CH2:36]3)[S:5](=[O:23])(=[O:22])[N:6]([CH:19]([CH3:21])[CH3:20])[CH2:7][C:8]=2[CH:13]=1)(=[O:16])=[O:15])[CH3:18]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 110530726-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 18332422HCID 18332422, compound

Product 1

HCID 18332434HCID 18332434, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(2-Chloroethyl)-3,4-dihydro-6-(ethylsulfonyl)-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide (1.03 g, 0.0027 mol), 6-fluoro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.706 g, 0.0033 mol), sodium iodide (0.408 g, 0.0027 mol) and sodium bicarbonate (1.586 g, 0.015 mol) were suspended in water (75 ml). The reaction mixture was heated at reflux overnight. The product mixture was then cooled to room temperature. The product was extracted into ethyl acetate (3×50 ml). The organic extracts were combined, washed with water (150 ml), dried (MgSO4) and concentrated in vacuo to afford 3,4-dihydro-6-ethylsulfonyl-1-[2-[4-(6-fluoro-1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinyl]ethyl]-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide. δ(1H NMR, DMSO, ppm): 1.10 (9H, m), 2.50 (2H, m), 2.80 (4H, m), 3.25 (4H, m), 4.10 (3H, m), 4.90 (2H, s), 6.10 (1H, s), 6.90 (1H, dt), 7.20 (1H, dd), 7.35 (1H, d), 7.40 (1H, d), 7.80 (3H, m), 11.20 (1H, s).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. extractionThe product was extracted into ethyl acetate (3×50 ml)
  4. washwashed with water (150 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1227423fb5b54960b29e1bec4e3330c3
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

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