1-Bromo-2-fluorobenzene → HCID 11600842, compound

HRID 888172Notes

Reaction equation

HRID 888172 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].[CH3:9][C@@H:10]1[CH2:15][NH:14][CH2:13][CH2:12][NH:11]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[F:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:14]1[CH2:13][CH2:12][NH:11][C@H:10]([CH3:9])[CH2:15]1

Participants

7

Reactant 3

HCID 612591-Bromo-2-fluorobenzeneHCID 73304342-Methylpiperazine, (R)-HCID 23676156Sodium t-butoxide

Product 1

HCID 11600842HCID 11600842, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 1-bromo-2-fluorobenzene (5.0 g, 28.5 mmol), (R)-2-methylpiperazine (3.15 g, 31.3 mmol) and sodium-tert-butoxide (4.0 g, 42 mmol) in dry toluene (100 mL) under nitrogen was added Pd(OAc)2 (250 mg, 1.1 mmol) followed by BINAP (750 mg, 1.2 mmol). The reaction mixture was then refluxed for 16 h and cooled. The reaction mixture was washed with water, dried and evaporated to a residue. The residue was purified by chromatography using chloroform/methanol (8/2) as eluent to afford the title compound as a liquid (3.0 g, 55%). TLC-Chloroform/Methanol (9/1); Rf: 0.25. HPLC purity: 95%.

Workup

  1. temperatureThe reaction mixture was then refluxed for 16 h
  2. temperaturecooled
  3. washThe reaction mixture was washed with water
  4. customdried
  5. customevaporated to a residue
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-c18f1ee93c1544f280b4a1ccdfb47664
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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