N,1-dihydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbimidoyl chloride → HCID 71571899, compound

HRID 532185Notes

Reaction equation

HRID 532185 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])[CH:21]=[C:20]([Cl:30])[C:19]=1[O:31][CH3:32]>CN(C=O)C>[Cl:17][C:18]1[CH:23]=[C:22]([C:24]2([C:26]([F:29])([F:27])[F:28])[O:1][N:2]=[C:3]([C:4]3[CH:15]=[CH:14][C:7]4[B:8]([OH:13])[O:9][C:10]([CH3:12])([CH3:11])[C:6]=4[CH:5]=3)[CH2:25]2)[CH:21]=[C:20]([Cl:30])[C:19]=1[O:31][CH3:32]

Participants

4

Reactant 2

HCID 86685046N,1-dihydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbimidoyl chlorideHCID 866850631,3-Dichloro-2-methoxy-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Product 1

HCID 71571899HCID 71571899, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of crude compound N,1-dihydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxa-borole-5-carbimidoyl chloride (0.29 g, 1.23 mmol) and 1,3-dichloro-2-methoxy-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (0.4 g, 1.48 mmol) in DMF (10 mL) at rt was added TEA (0.51 mL, 3.67 mmol). The reaction mixture was stirred for 12 h, poured into ice-water and extracted with EA. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by prep-TLC eluted with PE-EA (3:2) and then purified by preparative TLC to give the title compound (110 mg, yield 15.6%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.27 (s, 1 H), 7.82-7.75 (m, 5 H), 4.46 (d, J=18.4 Hz, 1 H), 4.36 (d, J=18.4 Hz, 1 H), 3.93 (s, 3 H), 1.53 (s, 6 H) ppm; MS: m/z=472 (M−1, ESI−).

Workup

  1. extractionextracted with EA
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified
  7. washby prep-TLC eluted with PE-EA (3:2)
  8. custompurified by preparative TLC

Sources & evidence

ORD record
ord-c4199bde08e244d08a6f2b1e3a3218e3
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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