Bromobenzene → HCID 11580091, compound

HRID 2065462Notes

Reaction equation

HRID 2065462 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[CH:15]1([NH:21][C:22]([C@H:24]2[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]2)=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.O1CCOCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:15]1([NH:21][C:22]([C@H:24]2[CH2:29][CH2:28][CH2:27][N:26]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:25]2)=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

7

Reactant 5

HCID 7961BromobenzeneHCID 312751,4-DioxaneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 66742803HCID 66742803, compound

Product 1

HCID 11580091HCID 11580091, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A mixture of bromobenzene (13 μL, 0.00012 mol), (3S)—N-cyclohexylpiperidine-3-carboxamide trifluoroacetate (40 mg, 0.0001 mol), sodium tert-butoxide (28 mg, 0.00030 mol), palladium acetate (0.8 mg, 0.000004 mol) and 2-(di-tert-butylphosphino)biphenyl (1 mg, 0.000004 mol) was vacuumed and charged with nitrogen. To the mixture was added 1,4-dioxane (1 mL, 0.01 mol) and the resulting mixture was refluxed overnight. After cooling, the mixture to ambient temperature the inorganics were filtered and the filtrate was adjusted with TFA to pH=7.0. The crude product was chromatographed by combiflash (ethyl acetate in hexanes: 60%) to afford the desired product. LCMS: m/z 287.3 (M+H)+.

Workup

  1. additioncharged with nitrogen
  2. temperaturethe resulting mixture was refluxed overnight
  3. temperatureAfter cooling
  4. filtrationthe mixture to ambient temperature the inorganics were filtered
  5. customThe crude product was chromatographed by combiflash (ethyl acetate in hexanes: 60%)

Sources & evidence

ORD record
ord-06064d9dc4a5432d88eb9ff276e4f81a
Source dataset
uspto-grants-2012_10
Patent number
US08288417B2

Reaction notes

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