tert-butyl N-(prop-2-yn-1-yl)carbamate → Tert-butyl({1-[(6-bromopyridin-2-yl)methyl]-1h-1,2,3-triazol-4-yl}methyl)carbamate

HRID 386044Notes

Reaction equation

HRID 386044 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[N:6]=1)=[N+:2]=[N-:3].[CH2:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:13]#[CH:14].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+]>[C:18]([O:17][C:16](=[O:22])[NH:15][CH2:12][C:13]1[N:3]=[N:2][N:1]([CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[N:6]=2)[CH:14]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 3

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 23667548Sodium AscorbateHCID 453574032-(Azidomethyl)-6-bromopyridine

Product 1

HCID 59526311Tert-butyl({1-[(6-bromopyridin-2-yl)methyl]-1h-1,2,3-triazol-4-yl}methyl)carbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6386tert-ButanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-(Azidomethyl)-6-bromopyridine (Example 470 Step 1) (700 mg, 3.29 mmol) and tert-butyl prop-2-yn-1-ylcarbamate (510 mg, 3.29 mmol) were combined in t-BuOH (6.0 mL) and water (3.0 mL). CuSO4.5H2O (41 mg, 0.16 mmol) in water (1.0 mL) was added, followed by sodium ascorbate (130 mg, 0.66 mmol) in water (2.0 mL). The reaction was stirred at room temperature for 2 h. The solution was subsequently diluted with saturated NaHCO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Purification by flash chromatography (40-100% EtOAc/hexanes) afforded the title compound as a colorless solid.

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (40-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-520ee6de75a6473996841c3bfcdbc32c
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

Loading…