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

HRID 253953Notes

Reaction equation

HRID 253953 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-4551e5c200e24a60b34dba623c5b672d
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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