1H-Indazole → HCID 9878877, compound

HRID 2121863Notes

Reaction equation

HRID 2121863 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([NH:17][CH2:18][CH:19]([OH:21])[CH3:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:22]1C2C(=CC=CC=2)C=N1.N([O-])=O.[Na+]>[Zn]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:12]([CH:13]=[N:22][N:17]2[CH2:18][CH:19]([OH:21])[CH3:20])=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 92211H-IndazoleHCID 22247174HCID 22247174, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 9878877HCID 9878877, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

The product of Step C (202.7 g, 0.71 mol) was treated as described for Steps C and D of Preparation 3. After the nitrosamine intermediate had been converted to a mixture of the desired indazole product and unreacted starting material (5:1), sodium nitrite (29.5 g, 0.43 mol) was added to renitrosate the starting material. Zinc dust (84 g, 1.28 mol) was then added in portions with cooling as described. When the starting material was consumed, the reaction mixture was worked up as described and combined with the product from another batch that started with 176 g of the product of Step C. The combined crude products were purified by chromatography (Biotage Kiloprep-250) to give a solid (226 g, 60%): 99% purity by HPLC.

Workup

  1. customas described for Steps C and D of Preparation 3
  2. additionwas added
  3. temperaturewith cooling
  4. customWhen the starting material was consumed
  5. customwere purified by chromatography (Biotage Kiloprep-250)

Sources & evidence

ORD record
ord-7e1a616fbee2491ea2fdcdb87ea6d594
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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