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

HRID 42778Notes

Reaction equation

HRID 42778 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH2:15][OH:16])[CH: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]=[CH:13][N:12]=[C:11]([CH2:15][O:16][S:24]([CH3:27])(=[O:26])=[O:25])[CH:10]=2)[O:5][CH2:6][CH2:7][O:8]1

Participants

7

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66929049[4-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-methanol

Product 1

HCID 86649481Methanesulfonic acid 4-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-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 [4-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-methanol (950 mg, 4.87 mmol) in dry CH2Cl2 (5 mL) was treated at 0° C. with Et3N (0.88 mL, 6.29 mmol) followed by DMAP (60 mg, 0.49 mmol) and Ms-Cl (0.49 mL, 6.15 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 yellow oil. LC-MS-conditions 02: tR=0.76 min, [M+H]+=274.30.

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-2384e6599ea749259f56e9210bce5bba
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

Loading…