Methanol → Methyl 5-bromo-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

HRID 897364Notes

Reaction equation

HRID 897364 reaction equation
[Br:1][C:2]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([OH:16])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.CO.O>C(Cl)(Cl)Cl>[Br:1][C:2]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([O:16][S:24]([C:21]2[CH:22]=[CH:23][C:18]([CH3:17])=[CH:19][CH:20]=2)(=[O:26])=[O:25])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 22343006Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate

Product 1

HCID 11339571Methyl 5-bromo-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a slurry of methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate (5.0 g, 17.66 mmol, prepared as in Example 113) in chloroform (20 mL) under nitrogen was added N,N,N-diisopropylethylamine (3.72 mL, 26.49 mmol). 4-Methylbenzenesulfonyl chloride (4.04 g, 21.20 mmol) was added over 5 minutes and the reaction was heated to 40 degrees C. and stirred one hour. The completed reaction was cooled to 25 degrees C. and 1:1 methanol:water was added to precipitate the product which was filtered, washed with more 1:1 methanol:water and dried in vacuo. This afforded the desired product as a solid.

Workup

  1. customThe completed reaction
  2. temperaturewas cooled to 25 degrees C
  3. customto precipitate the product which
  4. filtrationwas filtered
  5. washwashed with more 1:1 methanol
  6. dry with materialwater and dried in vacuo

Sources & evidence

ORD record
ord-f08812fb64f84c6e851afe36621b84f2
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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