2-(7-methyl-1H-indazol-5-ylmethylene)-succinic acid 1-methyl ester → 4-methoxy-3-((7-methyl-1H-indazol-5-yl)methyl)-4-oxobutanoic acid

HRID 1177758Notes

Reaction equation

HRID 1177758 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4](=[CH:9][C:10]1[CH:11]=[C:12]2[C:16](=[C:17]([CH3:19])[CH:18]=1)[NH:15][N:14]=[CH:13]2)[CH2:5][C:6]([OH:8])=[O:7]>C(OCC)(=O)C.CO.[Pd]>[CH3:1][O:2][C:3](=[O:20])[CH:4]([CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[C:17]([CH3:19])[CH:18]=1)[NH:15][N:14]=[CH:13]2)[CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 1

HCID 687076142-(7-methyl-1H-indazol-5-ylmethylene)-succinic acid 1-methyl ester

Product 1

HCID 184521154-methoxy-3-((7-methyl-1H-indazol-5-yl)methyl)-4-oxobutanoic acidYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-(7-methyl-1H-indazol-5-ylmethylene)-succinic acid 1-methyl ester (0.4440 g, 1.62 mmol) and 10% Pd/C (0.04 g) in ethyl acetate (15 mL) and methanol (5 mL) was hydrogenated in a Parr apparatus overnight at 50 psi. The reaction mixture was filtered through a pad of celite and the filtrate evaporated to give the desired product as a yellow solid (100%). Mass spec.: 277 (MH)+.

Workup

  1. customwas hydrogenated in a Parr apparatus overnight at 50 psi
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-f3b8abd1c66c4b94b1082077eac99b91
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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