Methyl iodide → Benzyl (5-iodo-2-methoxypyridin-3-yl)carbamate

HRID 2283473Notes

Reaction equation

HRID 2283473 reaction equation
[OH:1][C:2]1[C:7]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]([I:19])=[CH:4][N:3]=1.[CH3:20]I>C(Cl)(Cl)Cl>[I:19][C:5]1[CH:6]=[C:7]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]([O:1][CH3:20])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178522276HCID 178522276, compound

Product 1

HCID 59432848Benzyl (5-iodo-2-methoxypyridin-3-yl)carbamateYield 53.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of benzyl (2-hydroxy-5-iodopyridin-3-yl)carbamate (16 g, 43 mmol) in CHCl3 (250 mL) was added Ag2CO3 (16.1 g, 58.4 g) and methyl iodide (27.0 mL, 434 mmol) in the dark, and the mixture stirred at RT for overnight. The solid was removed by filtration and the solvent was concentrated and purified by combi-flash (ISCO, 40g silica, UV254, 5:1 pet ether/ethyl acetate) to afford benzyl (5-iodo-2-methoxypyridin-3-yl)carbamate (8.85 g, 53% yield) as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.61 (br, 1H), 7.98 (d, J=1.6 Hz, 1H), 7.35-7.42 (m, 5H), 7.12 (s, 1H), 5.21 (s, 2H), 3.95 (s, 3H); MS (ES) m/z 385 (M+H).

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe solvent was concentrated
  3. custompurified by combi-flash (ISCO, 40g silica, UV254, 5:1 pet ether/ethyl acetate)

Sources & evidence

ORD record
ord-954555dc8a2c48878e91d4c82f3d31e9
Source dataset
uspto-grants-2015_09
Patent number
US09145393B2

Reaction notes

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