Potassium Carbonate → HCID 57527204, compound

HRID 1671806Notes

Reaction equation

HRID 1671806 reaction equation
Cl[C:2]1[N:7]=[C:6]2[S:8][C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[N:10][C:5]2=[CH:4][CH:3]=1.[C:15]1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:44]([O-:47])([O-])=[O:45].[K+].[K+]>CO.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:12]([NH:11][C:9]1[S:8][C:6]2[C:5]([N:10]=1)=[CH:4][CH:3]=[C:2]([C:44]([O:47][CH3:15])=[O:45])[N:7]=2)([CH3:14])[CH3:13]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 57527238HCID 57527238, compound

Product 1

HCID 57527204HCID 57527204, compoundYield 726.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-chloro-N-isopropylthiazolo[5,4-b]pyridin-2-amine (2.06 g, 9.05 mmol, 1.0 eq.), Pd(OAc)2 (0.2084 g, 0.928 mmol, 0.1 eq.), 1,3-bis(diphenylphosphino)propane (0.3775 g, 0.915 mmol, 0.1 eq.) and K2CO3 (1.90 g, 13.7 mmol, 1.5 eq.) in MeOH (24 mL) and DMF (12 mL) was stirred under an atmosphere of CO inside a bomb (42 psi) at 92° C. overnight. After cooling to room temperature, the reaction mixture was filtered through Celite and rinsed with MeOH. The filtrate was concentrated in vacuo, diluted with EtOAc and water. The layers were separated, and the organic layer was washed with brine and 10% aqueous LiCl, dried over Na2SO4, filtered and concentrated in vacuo. Silica gel chromatography using CH2Cl2:MeOH (10:0.1) as eluent afforded methyl 2-(isopropylamino)thiazolo[5,4-b]pyridine-5-carboxylate as a white solid (1.67 g, 74% yield).

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. washrinsed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiondiluted with EtOAc and water
  5. customThe layers were separated
  6. washthe organic layer was washed with brine and 10% aqueous LiCl
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-139b43f6a2754c89877d6acd6e0852a6
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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