Potassium Phosphate, Tribasic → 3-(6-Chloropyrazin-2-yl)pyrazolo[1,5-a]pyridine

HRID 1500761Notes

Reaction equation

HRID 1500761 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC1(C)C(C)(C)OB([C:44]2[CH:45]=[N:46][N:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=23)O1>CN(C=O)C.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]>[Cl:8][C:4]1[N:3]=[C:2]([C:44]2[CH:45]=[N:46][N:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=23)[CH:7]=[N:6][CH:5]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 785042,6-DichloropyrazineHCID 583859483-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine

Product 1

HCID 583034833-(6-Chloropyrazin-2-yl)pyrazolo[1,5-a]pyridineYield 33.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

2,6-Dichloropyrazine (0.316 g, 2.12 mmol), tris(dibenzylideneacetone)dipalladium (0), (0.097 g, 0.106 mmol), tricyclohexylphosphine (0.06 g, 0.212 mmol) and potassium phosphate (1.35 g, 6.36 mmol) were added to a suspension of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine (Preparation 27a, 0.518 g, 2.12 mmol)) in N,N′-dimethylformamide (10 mL). This mixture was subjected to microwave irradiation at 100° C. for 40 min. The reaction mixture was filtered through Celite®, eluting with methanol, and the filtrate was evaporated. The resulting residue was purified by flash chromatography (2:8 to 3:7 ethyl acetate/hexane) to yield the title compound (0.162 g, 33%, two steps) as a pale yellow solid.

Workup

  1. customirradiation at 100° C. for 40 min
  2. filtrationThe reaction mixture was filtered through Celite®
  3. washeluting with methanol
  4. customthe filtrate was evaporated
  5. customThe resulting residue was purified by flash chromatography (2:8 to 3:7 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f37ecd45dff4442b88a805aa14b296bb
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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