Triethylamine → 1-(2-Fluoro-5-methylphenyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

HRID 1677643Notes

Reaction equation

[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[O:3]1.C(N(CC)CC)C.[F:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=1[N:32]=[C:33]=[O:34]>CN(C)C1C=CN=CC=1.O1CCCC1>[F:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=1[NH:32][C:33]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1)=[O:34]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1.45 g of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine, 1.86 mL of triethylamine and 162 mg of 4-dimethlaminopyridine in 150 mL of tetrahydrofuran at 20° C. is added 1 g of 1-fluoro-2-isocyanato-4-methylbenzene. The reaction is stirred for 3 hours 30 minutes at 60° C., and then concentrated to dryness under reduced pressure. The residue is taken up in a mixture of water and dichloromethane. The organic phase is washed with 1N HCl solution and then dried over magnesium sulfate and concentrated to dryness under reduced pressure. 2.13 g of a white powder of 1-(2-fluoro-5-methylphenyl)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea are obtained, the characteristics of which are as follows:

Workup

concentrationconcentrated to dryness under reduced pressure
additionThe residue is taken up in a mixture of water and dichloromethane
washThe organic phase is washed with 1N HCl solution
dry with materialdried over magnesium sulfate
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-d425f20709ef45738ff20da1a6fbada5
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008322B2

Reaction notes

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