1-Bromo-4-fluorobenzene → HCID 21090461, compound

HRID 350849Notes

Reaction equation

HRID 350849 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.[CH3:9][C:10]([O:13][C:14]([NH:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:15])([CH3:12])[CH3:11].CC(C)([O-])C.[K+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C([O-])(O)=O.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1C=CC(C)=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:20]2[CH2:19][CH2:18][CH:17]([NH:16][C:14](=[O:15])[O:13][C:10]([CH3:11])([CH3:9])[CH3:12])[CH2:22][CH2:21]2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 99931-Bromo-4-fluorobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 21090461HCID 21090461, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

To a p-xylene (25 mL) solution containing 4-fluorobromobenzene (275 μL, 2.5 mmol, 1.0 eq), 4-N—BOC-aminopiperidine (1.0 g, 4.99 mmol, 2.0 eq), and potassium t-butoxide (393 mg, 3.5 mmol, 1.4 eq) was added palladium (II) acetate (6 mg, 1 mol %) and tri-t-butylphosphine (20 mg, 4 mol %). The resulting mixture was then heated to 120° C. for 4 h at which time it was poured into a sat. NaHCO3 solution and extracted (2×) with EtOAc. The combined extracts were dried over MgSO4 and concentrated in vacuo. The resulting oil was purified via column chromatography using 1:1 hexanes/EtOAc as the mobile phase. Isolated 485 mg (1.65 mmol, 67% yield).

Workup

  1. extractionextracted (2×) with EtOAc
  2. dry with materialThe combined extracts were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting oil was purified via column chromatography
  5. customIsolated 485 mg (1.65 mmol, 67% yield)

Sources & evidence

ORD record
ord-b71d7d75db4548bcade8dfb36e1afaef
Source dataset
uspto-grants-2007_02
Patent number
US07183290B2

Reaction notes

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