Potassium Carbonate → HCID 86718575, compound

HRID 1480618Notes

Reaction equation

HRID 1480618 reaction equation
Br[C:2]1[CH:3]=[C:4]([Br:16])[C:5]2[O:10][CH2:9][N:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][C:6]=2[CH:15]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][C:19]=1[C:27]([F:30])([F:29])[F:28].C(=O)([O-])[O-].[K+].[K+]>CC(O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:16][C:4]1[C:5]2[O:10][CH2:9][N:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][C:6]=2[CH:15]=[C:2]([C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:20]=2)[CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27826714-Chloro-3-(trifluoromethyl)benzeneboronic acidHCID 86718560HCID 86718560, compound2×

Product 1

HCID 86718575HCID 86718575, compoundYield 20.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
72 °C

Procedure

A mixture of 6,8-dibromo-3-(tert-butyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine (Intermediate 6) (2.4 g, 6.92 mmol), (4-chloro-3-(trifluoromethyl)phenyl)boronic acid (1.628 g, 7.27 mmol), and potassium carbonate (1.434 g, 10.4 mmol) in 2-propanol (40 mL) and water (8 mL) was purged with nitrogen for 20 minutes. Tetrakis(triphenylphosphine)Pd (0) (336 mg, 0.29 mmol) was added and the resulting mixture heated at 72° C. for 3 h then the cooled reaction mixture concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried (MgSO4), filtered and concentrated under reduced pressure to give a solid that was re-crystallized from ethyl acetate to give 8-bromo-3-(tert-butyl)-6-(4-chloro-3-(trifluoromethyl)phenyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine (0.625 g).

Workup

  1. customwas purged with nitrogen for 20 minutes
  2. customthe cooled reaction mixture
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a solid
  10. customthat was re-crystallized from ethyl acetate

Sources & evidence

ORD record
ord-3f5ad991cd2a4b6383c4e6d99fb30d6d
Source dataset
uspto-grants-2016_08
Patent number
US09409893B2

Reaction notes

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