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

HRID 1890551Notes

Reaction equation

HRID 1890551 reaction equation
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

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 23371316HCID 23371316, compound

Product 1

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

Reagents, catalysts & solvents 3

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

Conditions

Temperature
120 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-457d2997448a4bbd824868adf76d00e1
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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