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

HRID 552889노트

반응식

HRID 552889 반응식
[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].[Li+].[BH4-]>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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 2-chloro-6-[(methylsulfonyl)(propyl)amino]isonicotinate (3.5 g, 11.5 mmol) in THF (50 mL) cooled to 0° C. was added LiBH4 (17.2 mL, 34.4 mmol, 2 M in THF). After 10 min, the reaction mixture was allowed to warm to rt and stirred for 3.5 h. The reaction mixture was carefully quenched with EtOAc, MeOH and water. Following dilution with EtOAc, the organic layer was extracted, washed with brine, dried over sodium sulfate and concentrated in vacuo to provide N-[6-chloro-4-(hydroxymethyl)pyridin-2-yl]-N-propylmethanesulfonamide which was used as is in the bromination step.

후처리

  1. customThe reaction mixture was carefully quenched with EtOAc, MeOH and water
  2. extractionthe organic layer was extracted
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-97725a5e32ea42428a7f70cd80a9f677
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951949B2

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