Tetrahydrofuran → HCID 20785162, compound

HRID 2064643Notes

Reaction equation

HRID 2064643 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10](C=CC(OC)=O)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:25]1CCC[CH2:26]1>O.I([O-])(=O)(=O)=O.[Na+].[Os](=O)(=O)(=O)=O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH:26]=[O:25])=[N:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 2

HCID 8028TetrahydrofuranHCID 696182895-Methoxy-3-(2-methoxycarbonyl-vinyl)-indazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 20785162HCID 20785162, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 23667635Sodium periodateSolvent

Procedure

A solution of 5-methoxy-3-(2-methoxycarbonyl-vinyl)-indazole-1-carboxylic acid tert-butyl ester [282 mg, Reference Example 21(a)] in tetrahydrofuran (4 ml) and water (1.5 ml) was treated with a solution of osmium tetroxide in water (54 μL, 4 wt %) and sodium periodate (400 mg). The reaction mixture was stirred at ambient temperature for 16 hours and then filtered. The filtrate was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate and then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and petrol (1:9, v/v) to yield 3-formyl-5-methoxy-indazole-1-carboxylic acid tert-butyl ester (162 mg) as a white solid. LC-MS (METHOD B): RT=2.97 minutes; 277 (M+H)+.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customthe residue was partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated
  6. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and petrol (1:9, v/v)

Sources & evidence

ORD record
ord-e680816c15664e2fb6b5d567e295d3a9
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

Loading…