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

HRID 1696372

반응식

HRID 1696372 반응식
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:58]1([S:55]([N:50]2[C:51]3[C:47](=[C:46]([CH2:65][C:64]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH:54]=[CH:53][CH:52]=3)[CH:48]=[CH:49]2)(=[O:57])=[O:56])[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e2a222192f044a6ba70d302dda4871a3
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163752B2

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