Water → HCID 86066890, compound

HRID 254161Notes

Reaction equation

HRID 254161 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][O:10][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:4]=1.[N-:30]=[N+:31]=[N-:32].[Na+].O>CN(C=O)C>[N:30]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][O:10][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:4]=1)=[N+:31]=[N-:32]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 66846510HCID 66846510, compound

Product 1

HCID 86066890HCID 86066890, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromomethyl-6-(triphenylmethoxymethyl)pyridine (3.04 g, 6.84 mmol) in DMF (25 mL) was treated with sodium azide (650 mg, 10 mmol) and stirred at room temperature for 20 h. The reaction was poured into water (100 mL), extracted with EtOAc (2×50 mL) and the combined organic phase was washed with brine (25 mL), dried (MgSO4) and concentrated in vacuo to give the product (2.75 g, 99%) as a yellow oil; IR νmax (Film)/cm−1 3060, 2103, 1679, 1594, 1448, 1096 and 706; NMR δH (400 MHz, CDCl3) 4.36 (2H, s), 4.39 (2H, s), 7.20-7.33 (10H, m), 7.49-7.52 (6H, m) and 7.72-7.80 (2H, m)

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washthe combined organic phase was washed with brine (25 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f1ddaea84f74258bca2e4c2a59078ff
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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