Triethylamine → Methanesulfonic acid 3-(5-bromo-pyridin-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl ester

HRID 747192Notes

Reaction equation

HRID 747192 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][OH:14])[O:10][N:9]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][O:14][S:23]([CH3:22])(=[O:25])=[O:24])[O:10][N:9]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 17954471[3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

Product 1

HCID 59749444Methanesulfonic acid 3-(5-bromo-pyridin-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl esterYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

[3-(5-Bromo-pyridin-2-yl)-4,5-dihydro-isoxazol-5-yl]-methanol (38.8 g, 150.5 mmol) was added to anhydrous dichloromethane (200 ml) followed by addition of triethylamine (29.2 ml, 210.7 mmol). The solution was cooled to 0° C. followed by dropwise addition of methane sulfonyl chloride (12.3 ml, 180.6 mmol). The reaction was stirred for 2 hours at 0° C. and then aqueous sodium bicarbonate (100 ml) was added. After further extraction with dichloromethane (2×100 ml), the organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the desired product (30.5 g).

Workup

  1. extractionAfter further extraction with dichloromethane (2×100 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-967564186375478b8f17d22fe808a783
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

Loading…