1h-Indazole-1-carboxylic acid,3-methoxy-5-nitro-,1,1-dimethylethyl ester → HCID 58710064, compound

HRID 2375927Notes

Reaction equation

HRID 2375927 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[C:10]([O:20][CH3:21])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=2)[C:10]([O:20][CH3:21])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 587100621h-Indazole-1-carboxylic acid,3-methoxy-5-nitro-,1,1-dimethylethyl ester

Product 1

HCID 58710064HCID 58710064, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-Methoxy-5-nitroindazole-1-carboxylic acid tert-butyl ester (0.33 g, 1.11 mmol) and palladium (10% wt) on carbon (0.24 g, 20% wt) were dissolved in EtOAc (25 mL). The flask was evacuated and filled with N2 (×5), then evacuated and filled with hydrogen (×10) and left over a weekend. The mixture was filtered over celite and the solvents removed in vacuo. Purification by column chromatography on silica gel (Jones, 20 g) loading in DCM and eluting in 5:1 Hexanes:EtOAc stepwise to 7:3 Hexanes:EtOAc yielded the title compound as a white powder. 1H NMR (400 MHz, CDCl3): δ=1.69 (s, 9H), 3.73 (brs, 2H), 4.15 (s, 3H), 6.85 (d, J=2.0 Hz, 1H), 6.91 (dd, J=8.8, 2.4 Hz, 1H), 7.74 (brs, 1H). MS (ES+): m/z 164.3 (65) [MH+](fragment ion, loss of Boc group).

Workup

  1. customThe flask was evacuated
  2. additionfilled with N2 (×5)
  3. customevacuated
  4. additionfilled with hydrogen (×10)
  5. waitleft over a weekend
  6. filtrationThe mixture was filtered over celite
  7. customthe solvents removed in vacuo
  8. customPurification by column chromatography on silica gel (Jones, 20 g) loading in DCM
  9. washeluting in 5:1 Hexanes

Sources & evidence

ORD record
ord-4aff233a61c1455bb3494f8ea04eda73
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

Loading…