Potassium Acetate → 10-(2-Fluoropyridin-3-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

HRID 1498092Notes

Reaction equation

HRID 1498092 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[CH:13][N:14]=[C:7]3[C:6]=2[CH:15]=1.[F:16][C:17]1[C:22](B(O)O)=[CH:21][CH:20]=[CH:19][N:18]=1.C([O-])(=O)C.[K+]>CN(C=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>[F:16][C:17]1[C:22]([C:2]2[CH:3]=[CH:4][C:5]3[O:11][CH2:10][CH2:9][N:8]4[CH:12]=[CH:13][N:14]=[C:7]4[C:6]=3[CH:15]=2)=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

7

Reactant 3

HCID 517044Potassium AcetateHCID 27832702-Fluoropyridine-3-boronic acidHCID 5820473910-Bromo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine

Product 1

HCID 5820489610-(2-Fluoropyridin-3-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 10-bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (140 mg, 0.53 mmol) in DMF (20 mL) and water (2 mL) was added 2-Fluoropyridine-3-boronic acid (89 mg, 0.632 mml), Potassium acetate (207 mg, 2.11 mmol) and Tetrakis(triphenylphosphine)palladium (30 mg, 0.0264 mmol). The reaction mixture was degassed for 5 minutes, and heated at 100° C. overnight. LCMS showed desired product peak. The reaction was allowed to cool to room temperature, diluted with EtOAc, and filtered through a thin pad of celite. The filtrate was washed with water followed by brine, dried over MgSO4 and concentrated. The crude residue was purified by Prep HPLC to provide 10-(2-fluoropyridin-3-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine. LC/MS (ESI+): m/z 282 (M+H)

Workup

  1. customThe reaction mixture was degassed for 5 minutes
  2. temperatureto cool to room temperature
  3. additiondiluted with EtOAc
  4. filtrationfiltered through a thin pad of celite
  5. washThe filtrate was washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude residue was purified by Prep HPLC

Sources & evidence

ORD record
ord-643ebc00771343279a23e4c6b04d9f7f
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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