Water → HCID 79733330, compound

HRID 1056617Notes

Reaction equation

HRID 1056617 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[Br:12][C:13]1[CH:19]=C[C:16]([NH2:17])=[CH:15][C:14]=1[CH3:20].[N:21]1C=CC=CC=1.O>C(Cl)Cl>[Br:12][C:13]1[C:14]([CH3:20])=[CH:15][C:16]([NH:17][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=2[F:11])=[N:21][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 233594-Bromo-3-methylanilineHCID 874382,6-Difluorobenzoyl chloride

Product 1

HCID 79733330HCID 79733330, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a (0° C.) cooled and stirred solution of 2,6-difluorobenzoyl chloride (500 mg, 2.83 mmol) in DCM (10 mL) was added 4-bromo-3-methylaniline (632 mg, 3.40 mmol) followed by the addition of pyridine (275 μL, 3.40 mmol). The resulting mixture was warmed to room temperature and stirred overnight. Water (10 mL) was then added to the above mixture and extracted with DCM (3×20 mL). The combined organic layers were washed with 10% aq.HCl (10 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum to afford 250 mg (28%) of the title compound as a white solid. 1HNMR (400 MHz, DMSO-d6) δ 11.44 (s, 1H, D2O exchangeable), 8.53 (s, 1H), 7.63 (s, 1H), 7.61-7.54 (m, 1H), 7.21 (t, J=7.0 Hz, 2H), 2.41 (m, 3H); (ESI-MS (m/z) 327, 329 [(MH)+ Br79,81]

Workup

  1. temperatureThe resulting mixture was warmed to room temperature
  2. extractionextracted with DCM (3×20 mL)
  3. washThe combined organic layers were washed with 10% aq
  4. dry with materialHCl (10 mL), dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-8d5b451d8b2740b8a8fcdb962194e37e
Source dataset
uspto-grants-2016_07
Patent number
US09399638B2

Reaction notes

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