Ethyl Acetate → [4-(3-Methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanol

HRID 1678796ノート

反応式

HRID 1678796 の反応式
[CH3:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[C:8]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:9]([C:15]4[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=4)=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][N:3]=1.[BH4-].[Na+].C(OCC)(=O)C>CO>[CH3:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[C:8]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:9]([C:15]4[CH:16]=[CH:17][C:18]([CH2:19][OH:20])=[CH:21][CH:22]=4)=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][N:3]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 594729414-(3-Methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzaldehyde

生成物 1

HCID 15979643[4-(3-Methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzaldehyde (5-2, 0.317 g, 0.870 mmol) in methanol (5 mL) was added sodium borohydride (0.033 g, 0.870 mmol) at 0° C. After 10 minutes, the reaction mixture was poured into ethyl acetate, and the organic layer was washed with a saturated solution of sodium bicarbonate, water, then brine, dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure. Purification by reverse phase chromatography (Waters Sunfire MSC18, 1% acetonitrile/0.1% trifluoroacetic acid/water→95% acetonitrile/0.1% trifluoroacetic acid/water) gave the title compounds as a solid. HRMS (M+H+): calculated=367.1554, observed=367.1547.

後処理

  1. washthe organic layer was washed with a saturated solution of sodium bicarbonate, water
  2. dry with materialbrine, dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. customPurification by reverse phase chromatography (Waters Sunfire MSC18, 1% acetonitrile/0.1% trifluoroacetic acid/water→95% acetonitrile/0.1% trifluoroacetic acid/water)

出典と根拠

ORDレコード
ord-34249ac51b7b48d591151540cfb524d5
出典データセット
uspto-grants-2011_08
特許番号
US08008317B2

反応ノート

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