Acetic Acid → HCID 22561859, compound

HRID 1839623Notes

Reaction equation

HRID 1839623 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]4[C:16](=[CH:17][CH:18]=3)[NH:15][N:14]=[C:13]4[NH2:19])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([OH:22])C.C(O)(=O)C.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CC(O)(C)C.[Zn]>[NH2:19][C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([C:5]3[CH:6]=[CH:7][CH:8]=[C:9]4[C:4]=3[CH2:3][C:2](=[O:22])[NH:1]4)[CH:11]=2)[NH:15][N:14]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 21124087PyridiniumtribromideHCID 22561707HCID 22561707, compound

Product 1

HCID 22561859HCID 22561859, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6386tert-ButanolSolvent

Procedure

To the suspension of 5-(1H-indol-4-yl)-1H-indazol-3-ylamine (0.82 g, 3.33 mmol) in t-BuOH:ethanol:acetic acid (20.5 mL:12 mL:6 mL) was added pyridinium tribromide (3.17 g, 9.9 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, it immediately became a dark pink color. Zinc dust (excess) was added to the reaction mixture portionwise. After stirring for one hour, the unreacted zinc was filtered off and the solvent was removed under reduced pressure. The residue was washed with ample of water. The solid was triturated with DCM to give 0.563 g (77%) of 4-(3amino-1H-indazol-5-yl)-1,3-dihydro-indol-2-one.

Workup

  1. stirringAfter stirring for one hour
  2. filtrationthe unreacted zinc was filtered off
  3. customthe solvent was removed under reduced pressure
  4. washThe residue was washed with ample of water
  5. customThe solid was triturated with DCM

Sources & evidence

ORD record
ord-4c259b644b094ec1ba61ebd001c94965
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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