Dimethylformamide → HCID 67440475, compound

HRID 1471584Notes

Reaction equation

HRID 1471584 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:20]=[CH:19][C:14]3[B:15]([OH:18])[O:16][CH2:17][C:13]=3[CH:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].I[CH2:22][CH3:23].CN(C)C=O.[H-].[Na+]>O>[CH2:22]([O:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:20]=[CH:19][C:14]3[B:15]([OH:18])[O:16][CH2:17][C:13]=3[CH:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 67327262HCID 67327262, compound

Product 1

HCID 67440475HCID 67440475, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-hydroxy-4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)benzonitrile (0.200 g, 0.749 mmol), iodoethane (0.182 mL, 2.25 mmol) and N,N-dimethylformamide (10 mL) under nitrogen balloon was put on an ice water bath. Sodium hydride (0.090 g, 2.25 mmol) was added and the mixture was stirred under nitrogen balloon at 0° C. for 15 minutes. The reaction was then stirred at room temperature for 2 hours. Water was added to quench the excess sodium hydride and the mixture was then neutralized using 1 M HCl. Water was added and the solution was extracted using ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was solidified by adding isopropylether. The precipitate was filtered and dried under reduced pressure to give 2-ethoxy-4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)benzonitrile (0.131 g, 59% yield). ES(−) MS m/z=294 (M−H)−; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33 (t, J=6.9 Hz, 3 H), 4.13 (q, J=7.0 Hz, 2 H), 4.95 (s, 2 H), 6.56 (dd, J=8.6, 1.9 Hz, 1 H), 6.89 (d, J=1.9 Hz, 1 H), 7.08 (dd, J=8.1, 1.6 Hz, 1 H), 7.14 (s, 1 H), 7.69 (d, J=8.6 Hz, 1 H), 7.77 (d, J=7.8 Hz, 1 H), 9.19 (s, 1 H).

Workup

  1. stirringThe reaction was then stirred at room temperature for 2 hours
  2. customto quench the excess sodium hydride
  3. additionWater was added
  4. extractionthe solution was extracted
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed under reduced pressure
  9. additionby adding isopropylether
  10. filtrationThe precipitate was filtered
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-e4984687df8244a1a947e0100f021da2
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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