Sodium borohydride → HCID 89443811、化合物

HRID 1771807ノート

反応式

HRID 1771807 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[CH:6][C:3]=1[CH:4]=O.[NH2:17][C:18]1[C:25]([F:26])=[CH:24][CH:23]=[C:22]([O:27][CH3:28])[C:19]=1[C:20]#[N:21].[BH4-].[Na+]>C1(C)C=CC=CC=1.CO>[F:26][C:25]1[C:18]([NH:17][CH2:4][C:3]2[CH:6]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=3)[CH:8]=[CH:9][C:2]=2[F:1])=[C:19]([C:22]([O:27][CH3:28])=[CH:23][CH:24]=1)[C:20]#[N:21]

参加物

6

反応物 3

HCID 4311764Sodium borohydrideHCID 463122473′,4-Difluoro[1,1′-biphenyl]-3-carboxaldehydeHCID 82012920HCID 82012920、化合物

生成物 1

HCID 89443811HCID 89443811、化合物収率 85.8%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

実験手順

To a solution of 2-fluoro-5-(3-fluorophenyl)benzaldehyde (505 mg, 2.32 mmol, 1.2 eq) and 2-amino-3-fluoro-6-methoxy-benzonitrile (320 mg, 1.93 mmol, 1 eq) in toluene (30 mL) was added 4 Å molecular sieves (10 g). The mixture was heated at reflux for 4 h, then filtered to remove the molecular sieves. The filtrate was concentrated and the residue obtained was dissolved in methanol (30 mL). NaBH4 (109.6 mg, 2.9 mmol, 1.5 eq) was added and the reaction stirred for 2 h at room temperature. The reaction was quenched by addition of water, and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 50:1) to give the title compound as an off-white solid (610 mg, 72%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 h
  3. filtrationfiltered
  4. customto remove the molecular sieves
  5. concentrationThe filtrate was concentrated
  6. customthe residue obtained
  7. customThe reaction was quenched by addition of water
  8. extractionthe aqueous layer was extracted with EtOAc
  9. washThe combined organic extracts were washed with brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated in vacuo
  13. customThe residue obtained
  14. customwas purified by column chromatography (petroleum ether:EtOAc, 50:1)

出典と根拠

ORDレコード
ord-88c98a9a917f43eaab3eeb1598336bd9
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

反応ノート

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