Diisopropylethylamine → methyl 1-(3-methoxypropyl)-1H-indazol-6-carboxylate

HRID 922448Notes

Reaction equation

HRID 922448 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[N:3]=1.C(N(C(C)C)CC)(C)C>CO.[Pd]>[CH3:19][O:18][CH2:17][CH2:16][CH2:15][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:6]=2)[CH:2]=[N:3]1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 59494402methyl 3-bromo-1-(3-methoxypropyl)-1H-indazole-6-carboxylate

Product 1

HCID 68632252methyl 1-(3-methoxypropyl)-1H-indazol-6-carboxylateYield 105.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 3-bromo-1-(3-methoxypropyl)-1H-indazole-6-carboxylate (3.0 g) and diisopropylethylamine (2.4 mL) in methanol (60 mL) was added 10% palladium on carbon catalyst (600 mg), and the mixture was stirred under hydrogen for 1 hour. An insoluble was filtered, and then the filtrate was concentrated under reduced pressure. The residue was dissolved in chloroform, sequentially washed with 10% hydrochloric acid water and saturated saline, and then concentrated under reduced pressure to give methyl 1-(3-methoxypropyl)-1H-indazole-6-carboxylate [REx(18-1)] (2.40 g) as a pale yellow oil.

Workup

  1. filtrationAn insoluble was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washsequentially washed with 10% hydrochloric acid water and saturated saline
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-86af1a61beda43b2970d08be6c0bcae1
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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