Cesium carbonate → tert-butyl (5-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)pentan-2-yl)carbamate

HRID 474244Notes

Reaction equation

HRID 474244 reaction equation
[CH3:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=2[OH:16])[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:24][CH2:25][CH2:26][CH:27]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH3:28]>CN(C=O)C>[CH3:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=2[O:16][CH2:24][CH2:25][CH2:26][CH:27]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])[CH3:28])[N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 666682322-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenolHCID 86668104Tert-butyl (5-bromopentan-2-yl)carbamate

Product 1

HCID 70348719tert-butyl (5-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)pentan-2-yl)carbamateYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenol (1.1 g, 5.00 mmol), cesium carbonate (2.44 g, 7.49 mmol) in DMF (20 mL) was added tert-butyl (5-bromopentan-2-yl)carbamate (2.45 g, 9.25 mmol) at room temperature. The reaction mixture was stirred at rt for 18 h while monitoring by TLC and LC-MS. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (250 mL) and washed with brine (2×100 mL). The organic layer was concentrated under reduced pressure and was purified by flash chromatography using a Teledyne ISCO instrument (40 g silica column, 2-3% of methanol in chloroform) to give tert-butyl (5-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)pentan-2-yl)carbamate (1.5 g, 74.1%) as a light brown solid. LC-MS (M+H)+=406.2. 1H NMR: (400 MHz, CDCl3) δ ppm 8.86 (1H, s), 8.09-8.07 (1H, d, J=8.8 Hz), 7.99-7.93 (2H, m), 4.33 (1H, br s), 4.27-4.24 (2H, t, J=6.4 Hz), 3.73 (1H, br s), 2.50 (3H, s), 1.98-1.95 (2H, m), 1.61-1.57 (2H, m), 1.44 (9H, s), 1.17-1.15 (3H, d, J=8 Hz).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (250 mL)
  3. washwashed with brine (2×100 mL)
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-52e283bc19964d0d9b287d4229e3bebb
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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