Potassium Carbonate → HCID 9948934, compound

HRID 1275702Notes

Reaction equation

HRID 1275702 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[N:6]=[C:5]2[C:18]1[O:19][C:20]([C:23](OC)=[O:24])=[CH:21][CH:22]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[N:6]=[C:5]2[C:18]1[O:19][C:20]([CH2:23][OH:24])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 9798341HCID 9798341, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9948934HCID 9948934, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 80 mg (0.23 mmol) of 5-amino-I-benzyl-3-(5-methoxycarbonyl-2-furyl)indazole in 5 ml of THF was added dropwise to 0.01 g (0.3 mmol) of lithium aluminum hydride in 5 ml of THF, and the mixture was stirred at RT. After 3 h, 10 ml of a 25% strength K2CO3 solution were added and stirring was continued for 30 min. The precipitate was filtered off with suction and extracted with boiling THF, the combined organic phases were dried and concentrated and the residue was chromatographed over silica gel using 95:5 dichloromethane/methanol. This gave 21 mg (29%) of the title compound. m.p.: 156° C.

Workup

  1. stirringstirring
  2. waitwas continued for 30 min
  3. filtrationThe precipitate was filtered off with suction
  4. extractionextracted with boiling THF
  5. customthe combined organic phases were dried
  6. concentrationconcentrated
  7. customthe residue was chromatographed over silica gel using 95:5 dichloromethane/methanol

Sources & evidence

ORD record
ord-bf1fea1354fb47abb5aabda9933128f7
Source dataset
uspto-grants-2000_12
Patent number
US06162819

Reaction notes

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