5-(4'-bromomethylbiphenyl-2-yl)-1-(4-nitrophenyl)-1H-tetrazole → HCID 19742909, compound

HRID 2254900Notes

Reaction equation

HRID 2254900 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([CH2:10][CH3:11])[C:3]=1[I:12].CC(C)([O-])C.[K+].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[N:37]([C:38]3[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=3)[N:36]=[N:35][N:34]=2)=[CH:23][CH:22]=1>C1COCC1>[CH2:10]([C:4]1[C:3]([I:12])=[C:2]([NH:1][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[N:37]([C:38]4[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=4)[N:36]=[N:35][N:34]=3)=[CH:25][CH:26]=2)[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=1)[CH3:11]

Participants

5

Reactant 3

HCID 199357915-(4'-bromomethylbiphenyl-2-yl)-1-(4-nitrophenyl)-1H-tetrazoleHCID 20094262HCID 20094262, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19742909HCID 19742909, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-amino-2,6-diethyl-3-iodopyridine (2 g) (obtained as described in Example 7 B) was added to a mixture of potassium t-butoxide (0.97 g) and 1,4,7,10,13,16-hexacyclooctadecane (200 mg) in THF (40 ml) and the mixture was stirred for 15 minutes. Compound E (4 g) was added and the mixture was stirred for 4 hours. Volatile material was removed by evaporation and the residue was dissolved in dichloromethane. The solution was washed with 0.1M citric acid solution and dried (MgSO4). Solvent was removed by evaporation and the residue was purified by flash chromatography eluting with dichloromethane/methanol (12:1 v/v) to give 2,6-diethyl-3-iodo-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methylamino]pyridine (F) (0.9 g) as a solid; NMR (CDCl3): 1.26(d of t, 6H), 2.70(q, 2H), 3.00(q, 2H), 4.35(d, 2H), 5.21(broad t, 1H), 6.10(s, 1H), 6.58(d, 2H), 6.79(d, 2H), 7.04(d, 2H), 7.37(m, 1H), 7.65(m, 2H), 7.86(d, 3H).

Workup

  1. stirringthe mixture was stirred for 4 hours
  2. customVolatile material was removed by evaporation
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washThe solution was washed with 0.1M citric acid solution
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed by evaporation
  7. customthe residue was purified by flash chromatography
  8. washeluting with dichloromethane/methanol (12:1 v/v)

Sources & evidence

ORD record
ord-3a0e994b60044120b94eeaa647cd658d
Source dataset
uspto-grants-1993_08
Patent number
US05236937

Reaction notes

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