1-Bromo-4-(methylsulphonyl)benzene → HCID 178504740, compound

HRID 1810070Notes

Reaction equation

HRID 1810070 reaction equation
Cl.[CH2:2]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH3:13])[CH2:9][CH2:8]1)[CH2:3][C:4]#[CH:5].Br[C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1CCCC1.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>[CH3:24][S:21]([C:18]1[CH:19]=[CH:20][C:15]([C:5]#[C:4][CH2:3][CH2:2][NH:6][C@H:7]2[CH2:8][CH2:9][C@H:10]([CH3:13])[CH2:11][CH2:12]2)=[CH:16][CH:17]=1)(=[O:23])=[O:22]

Participants

5

Reactant 2

HCID 770141-Bromo-4-(methylsulphonyl)benzeneHCID 178449164HCID 178449164, compound

Product 1

HCID 178504740HCID 178504740, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31268PyrrolidineSolvent

Conditions

Temperature
50 °C

Procedure

To a portion of the above but-3-ynyl-(trans-4-methyl-cyclohexyl)-amine hydrochloride (500 mg, 2.48 mmol) dissolved in pyrrolidine (2.5 mL) was added 1-bromo-4-methanesulfonyl-benzene (583 mg, 2.48 mmol) and the solution was degassed by bubbling nitrogen through for 10 min. Tetrakis(triphenylphosphine)palladium(0) (28 mg, 0.025 mmol) was added and the mixture was heated at 50° C. for 16 h before the volatiles were removed by evaporation and the residue purified by HPLC to yield the intermediate [4-(4-methanesulfonyl-phenyl)-but-3-ynyl]-(trans-4-methyl-cyclohexyl)-amine.

Workup

  1. customthe solution was degassed
  2. customby bubbling nitrogen through for 10 min
  3. customwere removed by evaporation
  4. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-5baae6834de347678a5a2146935a9a2d
Source dataset
uspto-grants-2013_01
Patent number
US08362049B2

Reaction notes

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