Triethylamine → HCID 71571671, compound

HRID 532159Notes

Reaction equation

HRID 532159 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9](/[CH:11]=[N:12]/[OH:13])=[CH:10][C:5]=2[C:4]([CH3:15])([CH3:14])[O:3]1.C1C(=O)N(Cl)C(=O)C1.[Cl:24][C:25]1[CH:30]=[C:29]([C:31]([C:33]([F:36])([F:35])[F:34])=[CH2:32])[CH:28]=[C:27]([Cl:37])[C:26]=1[CH3:38].CCN(CC)CC>CN(C=O)C>[Cl:24][C:25]1[CH:30]=[C:29]([C:31]2([C:33]([F:36])([F:34])[F:35])[O:13][N:12]=[C:11]([C:9]3[CH:8]=[CH:7][C:6]4[B:2]([OH:1])[O:3][C:4]([CH3:15])([CH3:14])[C:5]=4[CH:10]=3)[CH2:32]2)[CH:28]=[C:27]([Cl:37])[C:26]=1[CH3:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 86685048HCID 86685048, compoundHCID 89572652HCID 89572652, compound

Product 1

HCID 71571671HCID 71571671, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of (E)-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde oxime (62 mg, 0.3 mmol) and NCS (48 mg, 0.36 mmol) in DMF (2 mL) was stirred at rt overnight. To the mixture was added 1,3-dichloro-2-methyl-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (75 mg, 0.3 mmol) and Et3N (0.1 mL) and the mixture was stirred at rt for 4 h. It was partitioned between EA and H2O. The organic layer was washed with H2O, brine, dried over Na2SO4, concentrated under vacuum. The residue was purified to give the desired product (30 mg, 21.8% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.20 (s, 1H), 7.77-7.70 (m, 3H), 7.63 (s, 2H), 4.42 (d, J=18.4 Hz, 1H), 4.30 (d, J=18.4 Hz, 1H), 2.45 (s, 3H), 1.48 (d, J=2.4 Hz, 6H), ppm; HPLC purity: 98.6% at 220 nm and 98.9% at 254 nm; MS: m/z=458.5 (M+1, ESI+).

Workup

  1. stirringthe mixture was stirred at rt for 4 h
  2. customIt was partitioned between EA and H2O
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified

Sources & evidence

ORD record
ord-ddff74e2b87e457fa69d75837b0bd82b
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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