Sodium borohydride → 6-(5-hydroxymethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one

HRID 1774798노트

반응식

HRID 1774798 반응식
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]2[CH:19]=[CH:18][C:17]3[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH2:13][C:12]=3[N:11]=2)[CH:7]=[N:6][CH:5]=1.[BH4-].[Na+]>CO>[OH:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH2:13]3)[CH:7]=[N:6][CH:5]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 866791615-(5-Methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl ester

생성물 1

HCID 866791626-(5-hydroxymethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one수율 77.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of 5-(5-methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl ester (270 mg, 0.91 mmol) in MeOH (10 mL) was added sodium borohydride (300 mg, 8.0 mmol) at RT. After stirring overnight, the reaction mixture was quenched by adding water (5.0 mL). It was then concentrated in vacuo to give a light yellow oil. After extraction with EtOAc, the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give 6-(5-hydroxymethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one (190 mg, 77.6%) as a white solid. MS: 270.1 (M+H+).

후처리

  1. customthe reaction mixture was quenched
  2. additionby adding water (5.0 mL)
  3. concentrationIt was then concentrated in vacuo
  4. customto give a light yellow oil
  5. extractionAfter extraction with EtOAc
  6. washthe organic layer was washed with brine
  7. customdried over anhy
  8. filtrationNa2SO4, filtered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4da4bbcca8cb4bd9b732b932010d8649
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260408B2

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