Allyl iodide → HCID 66688630, compound

HRID 1895002Notes

Reaction equation

HRID 1895002 reaction equation
C(I)C=C.[C:5]([O:9][C:10]([N:12]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([C:23]3([CH2:28][CH:29]=[CH2:30])[CH2:27][CH2:26][NH:25][CH2:24]3)=[O:22])=[CH:18][CH:19]=2)[CH:14]=[N:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>CO.[Pd]>[C:5]([O:9][C:10]([N:12]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([C:23]3([CH2:28][CH:29]=[CH2:30])[CH2:27][CH2:26][NH:25][CH2:24]3)=[O:22])=[CH:18][CH:19]=2)[CH:14]=[N:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].[C:5]([O:9][C:10]([N:12]1[C:20]2[C:15](=[CH:16][C:17]([CH:21]([OH:22])[C:23]3([CH2:28][CH2:29][CH3:30])[CH2:27][CH2:26][NH:25][CH2:24]3)=[CH:18][CH:19]=2)[CH:14]=[N:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 2

HCID 11166Allyl iodideHCID 66687887HCID 66687887, compound

Product 2

HCID 66687887HCID 66687887, compoundHCID 66688630HCID 66688630, compoundYield 205.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(3-Allyl-pyrrolidine-3-carbonyl)-indazole-1-carboxylic acid tert-butyl ester was prepared as described in steps 3 and 4 of Example 1, but replacing benzyl bromide with allyl iodide. Pd/C (10%, Degussa catalyst type E101 NE/W, 100 mg) was added to a solution of 5-(3-allyl-pyrrolidine-3-carbonyl)-indazole-1-carboxylic acid tert-butyl ester (200 mg, 0.56 mmol) in MeOH (10 mL). The resulting mixture was stirred under hydrogen atmosphere (balloon pressure) for 2.5 hours. The reaction mixture was then filtered through a celite pad and the filtrate was evaporated under reduced pressure to give 207 mg of crude 5-[hydroxy-(3-propyl-pyrrolidin-3-yl)-methyl]-indazole-1-carboxylic acid tert-butyl ester as an off-white foam. This material was dissolved in toluene (8 mL) and activated manganese dioxide (85%, 240 mg, 2.80 mmol) was added. The resulting mixture was heated at 100° C. for 3 hours, then cooled to room temperature and filtered through a celite pad. The filtrate was evaporated under reduced pressure, and the resulting residue was purified by flash chromatography to give 86 mg of 5-(3-propyl-pyrrolidine-3-carbonyl)-indazole-1-carboxylic acid tert-butyl ester as a white foamy solid.

Workup

  1. filtrationThe reaction mixture was then filtered through a celite pad
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6adb4fa3fccb4efe875c1bcb71fa87d5
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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