Water → HCID 66846925, compound

HRID 76112Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[C:12]([OH:14])=[O:13].[H-].[Na+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[CH2:17]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[C:6]([C:12]([O:14][CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:3][CH:4]=2)=[O:13])=[N:7]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of 5-methoxy-1H-indazole-3-carboxylic acid (21.5 g; 0.11 mol) and 60% NaH (10.5 g; 0.44 mol) in N,N-dimethylformamide (DMF) (200 ml) was stirred at 70° C. for 1 hour. Benzyl chloride (32.9 g; 0.26 mol) was then added slowly to the suspension and the mixture was stirred at 70° C. for 4 hours. The reaction was stopped by cooling the mixture to room temperature and pouring the mixture into water and ice. The product was extracted with ethyl acetate (3×250 ml). The combined organic phases were concentrated under reduced pressure. The crude residue thus obtained was purified by successive crystallizations from 95° ethanol, to give 18 g of benzyl 1-benzyl-5-methoxy-1H-indazole-3-carboxylate with a melting point of 107-109° C.

Workup

stirringthe mixture was stirred at 70° C. for 4 hours
temperatureby cooling the mixture to room temperature
extractionThe product was extracted with ethyl acetate (3×250 ml)
concentrationThe combined organic phases were concentrated under reduced pressure
customThe crude residue thus obtained
customwas purified by successive crystallizations from 95° ethanol

Sources & evidence

ORD record: ord-9428a551802343f1bce87862f2ba4e65
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835481B2

Reaction notes

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