Sodium Hydroxide → HCID 86754290, compound

HRID 583081Notes

Reaction equation

HRID 583081 reaction equation
O=[CH:2][CH2:3][N:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][NH:6][S:5]1(=[O:15])=[O:14].[F:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21]([C:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH:27]=3)=[CH:22][NH:23]2)=[CH:19][CH:18]=1.N1C=CC=CC=1.B.[OH-].[Na+]>CO.O>[F:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21]([C:26]3[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][N:4]4[C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=5[CH:7]=[N:6][S:5]4(=[O:15])=[O:14])[CH2:28][CH:27]=3)=[CH:22][NH:23]2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 2723995Borane;pyridineHCID 110530726-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 17777160HCID 17777160, compound

Product 1

HCID 86754290HCID 86754290, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a dry 100 ml round bottomed flask containing powdered molecular sieves 4A (1.5 g) was added 3,4-dihydro-1-(2-oxoethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide (0.8 g, 3.54 mmol) in methanol (30 ml)and 4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydropyridine (0.76 g) dissolved in methanol (10 ml). Borane-pyridine (1 ml) was added after 1 hour and the solution stirred overnight. 5 MHCl (10 ml) was added followed by 50% sodium hydroxide solution(5 ml) and water(5 ml). Solution was filtered through celite and ethyl acetate(3×50 ml) added. The organics were collected, washed with water, dried, filtered and the solvent removed in vacuo. Column chromatography through flash silica eluting with ethyl acetate/hexane gave product, 3,4-dihydro-(1-(2-[4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydro-1-pyridyl]-1-ethyl}-1H-2,1,3-benzothiadiazine-2,2-dioxide, m.p. 183-185° C.

Workup

  1. addition5 MHCl (10 ml) was added
  2. filtrationSolution was filtered through celite and ethyl acetate(3×50 ml)
  3. additionadded
  4. customThe organics were collected
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4a999376a4aa4b2aa45e9e9bc6fe3a49
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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