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Water → 2-bromo-4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridine

HRID 2402377
Notes
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Reaction equation

HRID 2402377 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]#[CH:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([CH2:16][N:17]=[N+:18]=[N-:19])=[CH:14][CH:13]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].O>CCOC(C)=O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Cu+2].CC(O)(C)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[N:19]=[N:18][N:17]([CH2:16][C:15]3[CH:20]=[CH:21][C:12]([O:11][CH3:10])=[CH:13][CH:14]=3)[CH:9]=2)[CH:5]=[CH:4][N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 109317671-(Azidomethyl)-4-methoxybenzeneHCID 234368102-Bromo-4-ethynylpyridineHCID 23667548Sodium Ascorbate

Product 1

HCID 866808002-bromo-4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridineYield 77%

Reagents, catalysts & solvents 3

HCID 24463
Copper sulfate pentahydrate
Catalyst
HCID 6386tert-ButanolSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing 2-bromo-4-ethynylpyridine (1 g, 5.49 mmol) was added 4-methoxybenzyl azide (896 mg, 5.49 mmol), CuSO4(H2O)5 (137 mg, 0.549 mmol), sodium ascorbate (544 mg, 2.75 mmol), water (13.7 mL) and tBuOH (13.7 mL) and the reaction was stirred for 16 h at rt. The reaction was diluted with EtOAc (50 mL) and washed with saturated aqueous NaHCO3 (1×20 mL) and brine (1×20 mL). The organic phase was dried (MgSO4), filtered, and purified by silica gel chromatography using a gradient solvent system of 30-70% EtOAc/Hexanes. Concentration of the product fractions yielded 2-bromo-4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridine (1.46 g, 77%) as a white powder. MS ESI calcd for C15H13BrN4O [M+H]+ 345, found 345.

Workup

  1. washwashed with saturated aqueous NaHCO3 (1×20 mL) and brine (1×20 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-0541a742e24e42b4876e9b0f0320e7ee
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08796310B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes