Sodium borohydride → 6-(tert-butyl)-2-(3-chloro-2-(hydroxymethyl)phenyl)-8-fluorophthalazin-1(2H)-one

HRID 407608ノート

反応式

HRID 407608 の反応式
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH:19]=[O:20])[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH2:19][OH:20])[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 594738282-(6-(tert-butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-chlorobenzaldehyde

生成物 1

HCID 594737806-(tert-butyl)-2-(3-chloro-2-(hydroxymethyl)phenyl)-8-fluorophthalazin-1(2H)-one収率 76.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-chloro-benzaldehyde 101i (519 mg, 1.4 mmol) was dissolved in DCM (2 mL) with stirring at room temperature, and then 1 mL of iPA was added to the solution. The resulting solution was cooled to 4° C., and NaBH4 (27 mg, 0.7 mmol) was added in one portion. After 30 min stirring, the reaction was quenched by adding H2O (2 mL). The aqueous layer was extracted with CH2Cl2 (2×5 mL), washed with brine and dried over MgSO4. The filtrate was concentrated to give a residue which was purified by silica gel chromatography eluting with 0-20% EtOAc/CH2Cl2 to furnish 101j as a white solid (385 mg, 72%). MS: [M+H]+: 361

後処理

  1. addition1 mL of iPA was added to the solution
  2. temperatureThe resulting solution was cooled to 4° C.
  3. stirringAfter 30 min stirring
  4. customthe reaction was quenched
  5. additionby adding H2O (2 mL)
  6. extractionThe aqueous layer was extracted with CH2Cl2 (2×5 mL)
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationThe filtrate was concentrated
  10. customto give a residue which
  11. customwas purified by silica gel chromatography
  12. washeluting with 0-20% EtOAc/CH2Cl2

出典と根拠

ORDレコード
ord-696a92880fcb4923a8bdd10fc61b7446
出典データセット
uspto-grants-2014_06
特許番号
US08754077B2

反応ノート

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