N,1-dihydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbimidoyl chloride → HCID 71572118, compound

HRID 532210Notes

Reaction equation

HRID 532210 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:15]=[CH:14][C:7]2[B:8]([OH:13])[O:9][C:10]([CH3:12])([CH3:11])[C:6]=2[CH:5]=1.[Cl:17][C:18]1[CH:23]=[C:22]([C:24]([C:26]([F:29])([F:28])[F:27])=[CH2:25])[C:21]([Cl:30])=[C:20]([Cl:31])[C:19]=1[Cl:32]>CN(C=O)C>[CH3:11][C:10]1([CH3:12])[O:9][B:8]([OH:13])[C:7]2[CH:14]=[CH:15][C:4]([C:3]3[CH2:25][C:24]([C:22]4[CH:23]=[C:18]([Cl:17])[C:19]([Cl:32])=[C:20]([Cl:31])[C:21]=4[Cl:30])([C:26]([F:28])([F:27])[F:29])[O:1][N:2]=3)=[CH:5][C:6]1=2

Participants

4

Reactant 2

HCID 86685046N,1-dihydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbimidoyl chlorideHCID 86685078HCID 86685078, compound

Product 1

HCID 71572118HCID 71572118, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To the solution of N,1-dihydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbimidoyl chloride (0.526 mmol) in DMF (3 mL) was added 1,2,3,4-tetrachloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (245 mg, 0.789 mmol) and TEA (106 mg, 1.052 mmol) at rt. The mixture was stirred at 25° C. for 12 h, quenched with water, extracted with EA (3×10 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by prep-HPLC to give the final title compound 3,3-dimethyl-5-(5-(2,3,4,5-tetrachlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)benzo[c][1,2]oxaborol-1(3H)-ol (52 mg; yield 13%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 9.20 (s, 1H), 7.98 (s, 1H), 7.83 (s, 1H), 7.76-7.47 (d, J=3.2 Hz, 2H), 4.67-4.63 (d, J=18 Hz, 1H), 4.37-4.35 (d, J=18.8 Hz, 1H), 1.49 (s, 3H), 1.48 (s, 3H) ppm; MS: m/z=514 (M+1, ESI+).

Workup

  1. customquenched with water
  2. extractionextracted with EA (3×10 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-b5f3739eb9d54e90886d3d629e01ac9b
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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