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

HRID 556442Notes

Reaction equation

HRID 556442 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N:12]=[C:13]=[O:14].C(N(CC)CC)C.[CH3:22][C:23]1([CH3:37])[C:27]([CH3:29])([CH3:28])[O:26][B:25]([C:30]2[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=2)[O:24]1.CO>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13]([NH:34][C:33]1[CH:32]=[CH:31][C:30]([B:25]2[O:26][C:27]([CH3:29])([CH3:28])[C:23]([CH3:37])([CH3:22])[O:24]2)=[CH:36][CH:35]=1)=[O:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 161252301-(2-Fluoro-5-(trifluoromethyl)phenyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaYield 74.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

936 mg of 2-fluoro-5-trifluoromethylphenylisocyanate and then 0.64 ml of triethylamine are added to a solution of 1 g of 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)aniline in 15 ml of tetrahydrofuran, at ambient temperature. The reaction medium is stirred at ambient temperature for 18 h, and then treated with methanol and then, finally, evaporated to dryness under reduced pressure. The residue thus obtained is purified by chromatography on silica using, as eluent, a (99.5/0.5 then 90/10) methylene chloride/methanol mixture. The fractions containing the expected product are concentrated to dryness so as to give 1.45 g of 1-(2-fluoro-5-trifluoromethylphenyl)-3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]urea in the form of a white solid. MS (ES) MH+ m/z=425.

Workup

  1. customfinally, evaporated to dryness under reduced pressure
  2. customThe residue thus obtained
  3. customis purified by chromatography on silica using, as eluent
  4. additionThe fractions containing the expected product
  5. concentrationare concentrated to dryness so as

Sources & evidence

ORD record
ord-55bde56f466f4f11a5dc3fa4e91c26f9
Source dataset
uspto-grants-2011_11
Patent number
US08058290B2

Reaction notes

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