1-Methylpyrrolidine → 1-(3,3-Dimethylbutyl)-3-(2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

HRID 522708Notes

Reaction equation

HRID 522708 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:4][C:3]=1[NH:18][C:19](=O)[O:20]C(C)=C.[CH3:25][C:26]([CH3:31])([CH3:30])[CH2:27][CH2:28][NH2:29].CN1CCCC1>O1CCOCC1>[CH3:25][C:26]([CH3:31])([CH3:30])[CH2:27][CH2:28][NH:29][C:19]([NH:18][C:3]1[CH:4]=[C:5]([B:9]2[O:10][C:11]([CH3:16])([CH3:17])[C:12]([CH3:15])([CH3:14])[O:13]2)[C:6]([CH3:8])=[CH:7][C:2]=1[F:1])=[O:20]

Participants

5

Reactant 3

HCID 84541-MethylpyrrolidineHCID 197093,3-DimethylbutylamineHCID 86697010Prop-1-en-2-yl 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate

Product 1

HCID 898095371-(3,3-Dimethylbutyl)-3-(2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

Treat a solution of prop-1-en-2-yl 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (6.67 g, 19.90 mmol) in dioxane (60 mL) with 3,3-dimethylbutan-1-amine (2.42 g, 23.9 mmol) and 1-methylpyrrolidine (0.169 g, 1.99 mmol) and heat at 75° C. overnight. Cool the mixture to RT, collect the solid via filtration and wash with diethyl ether to obtain the title compound (6.62 g, 88% yield over two steps). MS (m/z): 379.2 (M+1).

Workup

  1. temperatureCool the mixture to RT
  2. customcollect the solid
  3. filtrationvia filtration
  4. washwash with diethyl ether

Sources & evidence

ORD record
ord-3d4fc877c07f48a9817f1efebe8c7025
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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