Potassium Carbonate → [4-(4-[1,2,3]Triazol-1-yl-but-1-enyl)-phenyl]-carbamic acid tert-butyl ester

HRID 1768045Notes

Reaction equation

HRID 1768045 reaction equation
[CH2:1]([N:5]1[CH:9]=[CH:8][N:7]=[N:6]1)[CH2:2][C:3]#[CH:4].B1C2CCCC1CCC2.[C:19]([O:23][C:24](=[O:33])[NH:25][C:26]1[CH:31]=[CH:30][C:29](I)=[CH:28][CH:27]=1)([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CN(C)C=O.C(OCC)(=O)C>[C:19]([O:23][C:24](=[O:33])[NH:25][C:26]1[CH:27]=[CH:28][C:29]([CH:4]=[CH:3][CH2:2][CH2:1][N:5]2[CH:9]=[CH:8][N:7]=[N:6]2)=[CH:30][CH:31]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 2773612tert-butyl N-(4-iodophenyl)carbamateHCID 184535221-But-3-ynyl-1H-[1,2,3]triazole

Product 1

HCID 69490216[4-(4-[1,2,3]Triazol-1-yl-but-1-enyl)-phenyl]-carbamic acid tert-butyl esterYield 33%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-but-3-ynyl-1H-[1,2,3]triazole (0.76 g, 6.3 mmol) in anhydrous THF (50 ml) is treated with 9-BBN (0.5 M in THF, 27.6 ml, 13.8 mmol) at 0° C. and stirred for 2 h. This mixture is added to a solution of (4-iodo-phenyl)-carbamic acid tert-butyl ester (2 g, 6.3 mmol), [Pd(PPh3)2]Cl2 (0.51 g, 0.63 mmol) and aqueous potassium carbonate (3M, 6.3 ml, 18.8 mmol) in N,N-dimethyl formamide (50 ml) and stirred for 2 h at 70° C. After cooling to room temperature ethyl acetate (100 ml) is added and the solution extracted with water (2×50 ml). The organic layer is concentrated and the crude product purified by flash column chromatography (ethyl acetate/heptane 3:1) and washing with diethyl ether to yield [4-(4-[1,2,3]triazol-1-yl-but-1-enyl)-phenyl]-carbamic acid tert-butyl ester as beige solid (0.65 g, 33%).

Workup

  1. stirringstirred for 2 h at 70° C
  2. additionis added
  3. extractionthe solution extracted with water (2×50 ml)
  4. concentrationThe organic layer is concentrated
  5. customthe crude product purified by flash column chromatography (ethyl acetate/heptane 3:1)
  6. washwashing with diethyl ether

Sources & evidence

ORD record
ord-4a5517bbb3114879b0b2ce36d7c3711b
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

Loading…