1H-Indazole → HCID 9878877, compound

HRID 1815944Notes

Reaction equation

HRID 1815944 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-2ae9cd23e3e04aa29d1c1c4754582435
Source dataset
uspto-grants-2005_04
Patent number
US06881749B2

Reaction notes

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