Potassium Carbonate → 1-Trityl-1,2,4-triazole-3-carboxylic acid ethyl ester

HRID 2103976Notes

Reaction equation

HRID 2103976 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=N[N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=1)=[O:5])[CH3:2].B1C2CCC[CH:31]1CCC2.C(=O)([O-])[O-].[K+].[K+].C(C1C=CC=CC=1I)(=O)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:31][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 2404312'-IodoacetophenoneHCID 670770332-Trityl-2H-tetrazol-5-carboxylic Acid Ethyl Ester

Product 1

HCID 574241681-Trityl-1,2,4-triazole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To Resin A (30 mg) was added THF (0.4 ml). To the mixture was added 9-BBN (0.5M in THF, 0.4 ml). The mixture was stirred at room temperature for 4 hours. To the mixture was added an aqueous solution of potassium carbonate (2M, 0.1 ml), 2-acetyliodobenzene (41 mg, 0.2 mmol) and PdCl2(dppf) (3 mg). The mixture was stirred at 50° C. for 20 hours. The obtained resin was washed with DMF, water, methanol and methylene chloride to give Resin B.

Workup

  1. stirringThe mixture was stirred at 50° C. for 20 hours
  2. washThe obtained resin was washed with DMF, water, methanol and methylene chloride

Sources & evidence

ORD record
ord-66b51324ab55474fb2a133c5c1f532f7
Source dataset
uspto-grants-2009_08
Patent number
US07576198B1

Reaction notes

Loading…