tert-Butyl acetate → tert-Butyl [1-(phenylsulfonyl)-1H-indol-4-yl]acetate

HRID 2426197Notes

Reaction equation

HRID 2426197 reaction equation
F[B-](F)(F)F.C(C1C=CC=C(C(C)C)C=1[N+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C=1)(C)C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[C:46]1[CH:54]=[CH:53][CH:52]=[C:51]2[C:47]=1[CH:48]=[CH:49][N:50]2[S:55]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)(=[O:57])=[O:56].[C:64]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])(=[O:66])[CH3:65]>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[C:68]([O:67][C:64](=[O:66])[CH2:65][C:46]1[CH:54]=[CH:53][CH:52]=[C:51]2[C:47]=1[CH:48]=[CH:49][N:50]2[S:55]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)(=[O:57])=[O:56])([CH3:71])([CH3:70])[CH3:69]

Participants

7

Reactant 4

HCID 10908tert-Butyl acetateHCID 2733832Lithium HexamethyldisilazideHCID 113750061,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborateHCID 220153114-Bromo-1-(phenylsulfonyl)-1H-indole

Product 1

HCID 57426198tert-Butyl [1-(phenylsulfonyl)-1H-indol-4-yl]acetate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazolium tetrafluoroborate (94 mg, 0.196 mmol), tris(dibenzylideneacetone)dipalladium (180 mg, 0.196 mmol), and lithium bis(trimethylsilyl)amide (1.37 M in t-BuOMe, 11.0 mL, 15.1 mmol) were added 4-bromo-1-(phenylsulfonyl)-1H-indole from Step A (2.20 g, 6.54 mmol), tert-butyl acetate (988 mg, 8.51 mmol), and toluene (15 mL). The resulting mixture was stirred at ambient temperature for 18 h then partitioned between Et2O (100 mL) and saturated aqueous NH4Cl (30 mL). The organic layer was washed with brine, then dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 85:15, to give the title compound. MS: m/z=316 (M—C4H7).

Workup

  1. customthen partitioned between Et2O (100 mL) and saturated aqueous NH4Cl (30 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-b5a5e35e42e64301b59aa3a3d1c3bfe6
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

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