Dimethyl Sulfoxide → HCID 89955073, 화합물

HRID 705349

반응식

HRID 705349 반응식
[C:1]([C:3]1[C:7]2[CH:8]=[C:9]([CH:17]3[CH2:19][CH2:18]3)[C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:11][C:6]=2[O:5][C:4]=1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:34][CH2:35][CH2:36][CH2:37][O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40].CS(C)=O>C(#N)C>[Si:39]([O:38][CH2:37][CH2:36][CH2:35][CH2:34][N:12]([C:10]1[C:9]([CH:17]2[CH2:18][CH2:19]2)=[CH:8][C:7]2[C:3]([C:1]#[N:2])=[C:4]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[O:5][C:6]=2[CH:11]=1)[S:13]([CH3:16])(=[O:15])=[O:14])([C:42]([CH3:43])([CH3:44])[CH3:45])([CH3:40])[CH3:41]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 4250746tert-Butyl(4-iodobutoxy)dimethylsilaneHCID 89955206N-[3-cyano-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-6-yl]methanesulfonamide

생성물 1

HCID 89955073HCID 89955073, 화합물수율 69%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

A mixture of Example 11A (0.1302 g, 0.352 mmol) and potassium carbonate (0.058 g, 0.422 mmol) in acetonitrile (2 mL) was heated at reflux for 30 minutes, then (4-iodobutoxy)-tert-butyldimethylsilane (0.122 g, 0.387 mmol) was added and the resultant mixture was stirred at reflux for 0.5 hour. The reaction mixture became thick so additional acetonitrile (2 mL) and dimethyl sulfoxide (2 mL) were added, and the resultant mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo to a yellow oil that was taken up in ethyl acetate (100 mL) and washed with 1 N aqueous H3PO4, 10% aqueous NaHCO3, and 10% aqueous NaCl. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo leaving a yellow oil. Purification on a silica gel column (12 g) eluting with a gradient of 10/90 ethyl acetate/hexane to 50/50 ethyl acetate/hexane over 20 minutes afforded the title compound (0.135 g, 69%).

후처리

  1. temperatureat reflux for 30 minutes
  2. temperatureat reflux for 0.5 hour
  3. additionwere added
  4. concentrationThe reaction mixture was concentrated in vacuo to a yellow oil that
  5. washwashed with 1 N aqueous H3PO4, 10% aqueous NaHCO3, and 10% aqueous NaCl
  6. dry with materialThe organic phase was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customleaving a yellow oil
  10. customPurification on a silica gel column (12 g)
  11. washeluting with a gradient of 10/90 ethyl acetate/hexane to 50/50 ethyl acetate/hexane over 20 minutes

출처 및 근거

ORD 기록
ord-cd9e9a774bb1432d824d84ce45d9b8f7
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173887B2

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