Isopropanol → HCID 57799652, compound

HRID 2101111Notes

Reaction equation

HRID 2101111 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:14][C:15]2[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=2)[N:3]=1.[CH:21]1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:25][CH:26]=1.[C:50]([O-])([O-:52])=[O:51].[Cs+].[Cs+].CC(O)C>CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[CH:26]([O:52][C:50]([C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:14][C:15]2[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=2)[N:3]=1)=[O:51])([CH3:25])[CH3:21]

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 10796Cesium carbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 57799674(1-chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine

Product 1

HCID 57799652HCID 57799652, compoundYield 828%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

An oven-dried flask was charged with 8.64 g (1-Chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine, 0.54 g Pd(OAc)2, 1.2 g dppp, 0.3 g Pd(PPh3)4, 24 g Cs2CO3 in the solution of 200 mL i-PrOH and 200 mL DMF, then evacuated and filled with CO (4 bar) three cycles. The mixture was shaken at r.t 2 h, at 50° C. 2 h, then 90° C. overnight. After reaction completed, the solvent was removed, and the residue was dissolved in ethyl acetate, washed with water, dried with Na2SO4. After removal of solvent, the residue was purified by the column chromatography on solica gel to give 8.2 g of 6-Methoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinoline-1-carboxylic acid isopropyl ester.

Workup

  1. customevacuated
  2. additionfilled with CO (4 bar) three cycles
  3. custom2 h
  4. custom90° C. overnight
  5. customAfter reaction
  6. customthe solvent was removed
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washwashed with water
  9. dry with materialdried with Na2SO4
  10. customAfter removal of solvent
  11. customthe residue was purified by the column chromatography on solica gel

Sources & evidence

ORD record
ord-2931e6dc042e4dbd9105db3b54c07152
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

Loading…