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

HRID 522540Notes

Reaction equation

HRID 522540 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][S:8]([NH2:11])(=[O:10])=[O:9].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.[CH2:42]([C:46]1[O:47][C:48]2[CH:54]=[CH:53][C:52](Br)=[CH:51][C:49]=2[CH:50]=1)[CH2:43][CH2:44][CH3:45]>O1CCOCC1.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]>[CH2:42]([C:46]1[O:47][C:48]2[CH:54]=[CH:53][C:52]([NH:11][S:8]([CH3:7])(=[O:10])=[O:9])=[CH:51][C:49]=2[CH:50]=1)[CH2:43][CH2:44][CH3:45]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 72879MethanesulfonamideHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 569260235-Bromo-2-butylbenzofuran

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 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

The following are placed in an equipped reactor under an argon atmosphere: 13 g of cesium carbonate (39.9 mmol), 3 g of methanesulfonamide (31.5 mmol), 250 mg of Pd(dba)2 (0.4 mmol) and 440 mg of 2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl (ligand L1) (1.04 mmol). 5.5 g of 2-n-butyl-5-bromobenzofuran (compound IX or II) (21.7 mmol) dissolved in 55 ml of dioxane are then added by syringe. The reaction medium is then stirred and heated at 100° C. for 24 hours.

Workup

  1. customThe following are placed in an equipped reactor under an argon atmosphere
  2. additionare then added by syringe

Sources & evidence

ORD record
ord-42e33efc87c94afe992f645d5d6a2124
Source dataset
uspto-grants-2016_05
Patent number
US09334254B2

Reaction notes

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