Nitrogen → Methanesulfonic acid 2-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-4-ylmethyl ester

HRID 42805Notes

Reaction equation

HRID 42805 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=[CH:11][N:10]=2)[O:8][CH2:7][CH2:6][O:5]1.CCN(CC)CC.[S:24](Cl)([CH3:27])(=[O:26])=[O:25]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:3][C:4]1([C:9]2[CH:14]=[C:13]([CH2:15][O:16][S:24]([CH3:27])(=[O:26])=[O:25])[CH:12]=[CH:11][N:10]=2)[O:5][CH2:6][CH2:7][O:8]1

Participants

7

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66929264HCID 66929264, compound

Product 1

HCID 86649484Methanesulfonic acid 2-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-4-ylmethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [2-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-4-yl]-methanol (530 mg, 2.72 mmol) in dry CH2Cl2 (5 mL) was treated at 0° C. with Et3N (0.50 mL, 3.56 mmol) followed by DMAP (34 mg, 0.27 mmol) and Ms-Cl (0.27 mL, 3.46 mmol). After stirring at rt for 2 h, the reaction was quenched with water (5 mL). The org. layer was dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (5:1 to 2:1 hept-EA) gave the title compound as a light brown oil. TLC:rf (1:2 hept-EA)=0.36.

Workup

  1. customthe reaction was quenched with water (5 mL)
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customPurification of the residue by FC (5:1 to 2:1 hept-EA)

Sources & evidence

ORD record
ord-411fc8efbb754c669621daca8b43d90f
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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