Lithium borohydride → N-[6-chloro-4-(hydroxymethyl)pyridin-2-yl]-N-propylmethanesulfonamide

HRID 1160183Notes

Reaction equation

HRID 1160183 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]([S:16]([CH3:19])(=[O:18])=[O:17])[CH2:13][CH2:14][CH3:15])[N:11]=1)[C:5](OC)=[O:6].[BH4-].[Li+]>C1COCC1>[Cl:1][C:2]1[N:11]=[C:10]([N:12]([CH2:13][CH2:14][CH3:15])[S:16]([CH3:19])(=[O:17])=[O:18])[CH:9]=[C:4]([CH2:5][OH:6])[CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57434730Methyl 2-chloro-6-[(methylsulfonyl)(propyl)amino]isonicotinate

Product 1

HCID 57775667N-[6-chloro-4-(hydroxymethyl)pyridin-2-yl]-N-propylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-chloro-6-[(methylsulfonyl)(propyl)amino]isonicotinate (3.52 g, 11.47 mmol) in THF (50 mL), cooled to 0° C., was added lithium borohydride (17.3 mL, 34.4 mmol, 2M THF) slowly via serynge. The reaction mixture was allowed to warm to RT by itself and stirred at RT for 3 h. The reaction mixture was carefully quenched with EtOAc, MeOH and water sequentially. The reaction mixture was diluted with EtOAc, the organic layer was separated, dried over sodium sulfate and concentrated in vacuo to give N-[6-chloro-4(hydroxymethyl)pyridin-2-yl]-N-propylmethanesulfonamide as a yellow thick oil. 1H NMR (400 MHz, CDCl3) δ 7.27 (s, 1H), 7.23 (s, 1H), 4.72 (s, 2H), 3.80 (t, J=8 Hz, 2H), 3.00 (s, 3H), 2.02 (s, 1H), 1.59-1.46 (m, 2H), 0.90 (t, J=7.6 Hz, 3H).

Workup

  1. customThe reaction mixture was carefully quenched with EtOAc, MeOH and water sequentially
  2. additionThe reaction mixture was diluted with EtOAc
  3. customthe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-525d6495442a452fb1d066a66e0c04ad
Source dataset
uspto-grants-2010_10
Patent number
US07816378B2

Reaction notes

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