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

HRID 876797노트

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HRID 876797 반응식
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

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 23371316HCID 23371316, 화합물

생성물 1

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

시약·촉매·용매 3

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

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7e189a47c0eb447bbd88da5b5e610b71
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987269B2

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