Diisopropylethylamine → HCID 68309091, compound

HRID 922459Notes

Reaction equation

HRID 922459 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:12]([N:14]([CH:22]3[CH2:24][CH2:23]3)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])=[CH:8][C:9]=2I)[N:4]([CH2:25][CH2:26][CH2:27][O:28][CH3:29])[N:3]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1.[Pd]>[CH:22]1([N:14]([CH:12]([C:7]2[CH:6]=[C:5]3[C:10]([CH:2]=[N:3][N:4]3[CH2:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:9][CH:8]=2)[CH3:13])[C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])[CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 68309090HCID 68309090, compound

Product 1

HCID 68309091HCID 68309091, compoundYield 25.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl N-{1-[3-bromo-4-iodo-1-(3-methoxypropyl)-1H-indazol-6-yl]ethyl}cyclopropylcarbamate (1.0 g) in 1,4-dioxane (20 mL) were added diisopropylethylamine (0.90 mL) and 10% palladium on carbon catalyst (200 mg), and the mixture was stirred under hydrogen for 42 hours. An insoluble was filtered, and then the filtrate was sequentially washed with aqueous saturated sodium hydrogen carbonate solution and saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→4/1) to give tert-butyl cyclopropyl{1-[1-(3-methoxypropyl)-1H-indazol-6-yl]ethyl}carbamate [REx(30-1)] (167 mg) as a colorless oil.

Workup

  1. filtrationAn insoluble was filtered
  2. washthe filtrate was sequentially washed with aqueous saturated sodium hydrogen carbonate solution and saturated saline
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→4/1)

Sources & evidence

ORD record
ord-07fc9f4e880044c6bd34e22e3135ddb2
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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