Sodium Hydroxide → 5-bromo-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine

HRID 1518507Notes

Reaction equation

HRID 1518507 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[C:15]([NH2:20])=[N:16][CH:17]=[CH:18][CH:19]=2)=[N:12][N:11]=[N:10]1.C1C(=O)N([Br:28])C(=O)C1.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+].[OH-].[Na+]>CC#N>[Br:28][C:18]1[CH:19]=[C:14]([C:13]2[N:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])[N:10]=[N:11][N:12]=2)[C:15]([NH2:20])=[N:16][CH:17]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 581800123-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine

Product 1

HCID 247624635-bromo-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(1-(2,3-Difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine was stirred in CH3CN (15 mL) and treated with NBS (2 eq). The reaction mixture was maintained at room temperature for 30 min. The reaction was subsequently poured into sat NaHCO3 solution and treated sequentially with 5 mL Na2S2O3 and 2 mL 6N NaOH. The solids were filtered, washed with water, and dried in vacuo to afford 5-bromo-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine, which was purified by silica gel chromatography. Using the same procedure, 5-bromo-3-(1-(2,3-dichlorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine and 5-bromo-3-(1-(3-chloro-2-fluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine can be produced from 3-(1-(2,3-dichlorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine and 3-(1-(3-chloro-2-fluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine, respectively.

Workup

  1. additionThe reaction was subsequently poured
  2. filtrationThe solids were filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ceed4c7f4b7e4ab2ac4293c9e624152c
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

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