Methanesulfonamide → N-(2-Butyl-1-benzofuran-5-yl)methanesulfonamide

HRID 522539Notes

Reaction equation

HRID 522539 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.[CH2:36]([C:40]1[O:41][C:42]2[CH:48]=[CH:47][C:46](Br)=[CH:45][C:43]=2[CH:44]=1)[CH2:37][CH2:38][CH3:39].C(OCC)(=O)C.CC1CCCCC1>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH2:36]([C:40]1[O:41][C:42]2[CH:48]=[CH:47][C:46]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:45][C:43]=2[CH:44]=1)[CH2:37][CH2:38][CH3:39]

Participants

7

Reactant 4

HCID 72879MethanesulfonamideHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 569260235-Bromo-2-butylbenzofuranHCID 66985183Ethyl acetate methylcyclohexane

Product 1

HCID 9878493N-(2-Butyl-1-benzofuran-5-yl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

The following are placed in a 20 ml tube predried in an oven: 2 equivalents of base and 1.5 equivalents of methanesulfonamide, 2 mol % of Pd(dba)2 and 5 mol % of 2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl (ligand L1). The tube is stoppered with a septum and placed under an inert atmosphere of argon, and 1 equivalent of 2-n-butyl-5-bromobenzofuran (compound IX or II) dissolved in 10 volumes of solvent is then added by syringe. The reaction medium is then stirred and heated to the reflux point of the solvent or at 100° C. for 24 hours, while monitoring the reaction progress by TLC (eluent: 20/80 ethyl acetate/methylcyclohexane) or by HPLC. At the end of the reaction, the reaction medium is diluted with ethyl acetate and then filtered while hot. The filtrate is then concentrated to give, when cold, crystallization of the desired compound I.

Workup

  1. customThe following are placed in a 20 ml tube
  2. custompredried in an oven
  3. dissolutiondissolved in 10 volumes of solvent
  4. additionis then added by syringe
  5. customAt the end of the reaction
  6. filtrationfiltered while hot
  7. concentrationThe filtrate is then concentrated
  8. customto give
  9. customwhen cold, crystallization of the desired compound I

Sources & evidence

ORD record
ord-d5aca24466ae447c8afc0586e14e049f
Source dataset
uspto-grants-2016_05
Patent number
US09334254B2

Reaction notes

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