Dimethylformamide → Thiazolo[5,4-b]pyridine-5-carbonitrile

HRID 876797ノート

反応式

HRID 876797 の反応式
Cl[C:2]1[N:7]=[C:6]2[S:8][CH:9]=[N:10][C:5]2=[CH:4][CH:3]=1.[CH3:11][N:12](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[N:10]1[C:5]2[C:6](=[N:7][C:2]([C:11]#[N:12])=[CH:3][CH:4]=2)[S:8][CH:9]=1

参加物

6

反応物 2

HCID 6228DimethylformamideHCID 23371316HCID 23371316、化合物

生成物 1

HCID 67305386Thiazolo[5,4-b]pyridine-5-carbonitrile

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
120 °C

実験手順

To an 8 mL screw cap vial equipped with a magnetic stirring bar were added 5-chlorothiazolo[5,4-b]pyridine (Q-4) (460 mg, 2.7 mmol), Zn(CN)2(316 mg, 2.7 mmol), Pd2(dba)3 (123 mg, 0.13 mmol), DPPF (150 mg, 0.27 mmol) and DMF (5 mL, wet, containing 1% of H2O). The vial was flushed with nitrogen, then sealed with the screw cap. The mixture was stirred at 120° C. for overnight, and then concentrated in vacuo. The resulting residue was purified by chromatography on silica gel to give the title compound (151 mg).

後処理

  1. customTo an 8 mL screw cap vial
  2. customequipped with a magnetic stirring bar
  3. customThe vial was flushed with nitrogen
  4. customsealed with the screw
  5. customcap
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-7e189a47c0eb447bbd88da5b5e610b71
出典データセット
uspto-grants-2015_03
特許番号
US08987269B2

反応ノート

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