Dimethylformamide → HCID 70975102, compound

HRID 57532Notes

Reaction equation

HRID 57532 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[CH:5]C=1N.C([O-])([O-])=O.[K+].[K+].CI.[CH3:26][N:27]([CH:29]=O)[CH3:28]>>[F:1][C:2]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[CH:5][C:29]=1[N:27]([CH3:26])[CH3:28]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 179061722-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 70975102HCID 70975102, compoundYield 93%

Conditions

Temperature
100 °C

Procedure

The mixture of 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (474 mg, 2 mmol), K2CO3 (828 mg, 6 mmol), and MeI (710 mg, 5 mmol) in DMF (10 mL), was stirred at 100° C. overnight. Then it was cooled and extracted by EA/H2O, the organic layer was combined, washed by brine, dried over anhydrous Na2SO4, and concentrated to give the crude compound in 93% yield. MS (m/z): 266 (M+H)+.

Workup

  1. temperatureThen it was cooled
  2. extractionextracted by EA/H2O
  3. washwashed by brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-64ccce987fae40de9af76a406ae4f158
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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