N-methoxy-N-methyl-1H-indazole-5-carboxamide → 1-(1H-Indazol-5-YL)propan-1-one

HRID 626213Notes

Reaction equation

HRID 626213 reaction equation
[CH3:1][CH2:2][Mg+].[Br-].CON(C)[C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][N:14]=[CH:13]2)=[O:9]>C1COCC1>[NH:15]1[C:16]2[C:12](=[CH:11][C:10]([C:8](=[O:9])[CH2:2][CH3:1])=[CH:18][CH:17]=2)[CH:13]=[N:14]1

Participants

4

Reactant 2

HCID 62814299N-methoxy-N-methyl-1H-indazole-5-carboxamideHCID 178461630HCID 178461630, compound

Product 1

HCID 391039921-(1H-Indazol-5-YL)propan-1-oneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

EtMgBr (3 M, 2.0 eq, 6.5 mL) was added to a solution of N-methoxy-N-methyl-1H-indazole-5-carboxamide (2 g, 1.0 eq) in dry THF at 0° C. Once addition was complete, the mixture was stirred for 2 h, and extracted by EtOAc. The extract was dried, concentrated, and purified by column chromatography with petroleum ether:EtOAc=1:1 to give the desired product (1.8 g, 95%). 1H NMR (400 MHz, CDCl3) δ 11.20 (s, 1H), 8.45 (s, 1H), 8.22 (s, 1H), 8.06 (d, J=8.0 Hz, 1H), 7.27 (d, J=8.0 Hz, 1H), 3.08 (q, J=7.6 Hz, 2H), 1.28 (t, J=7.6 Hz, 3H).

Workup

  1. additionOnce addition
  2. extractionextracted by EtOAc
  3. customThe extract was dried
  4. concentrationconcentrated
  5. custompurified by column chromatography with petroleum ether

Sources & evidence

ORD record
ord-597293e32251406fb9a2817880a7b594
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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