Dimethylformamide → HCID 72192144, 화합물

HRID 2174047노트

반응식

HRID 2174047 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:22])[C:5](I)=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2.CN([CH:26]=[O:27])C.C([Li])CCC>COC1CCCC1>[Cl:1][C:2]1[C:10]2[N:9]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=2[C:5]([CH:26]=[O:27])=[C:4]([CH3:22])[CH:3]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 867016707-chloro-4-iodo-5-methyl-1-tosyl-1H-indoleHCID 178418339Butyllithium2회

생성물 1

HCID 72192144HCID 72192144, 화합물

시약·촉매·용매 1

HCID 138539Cyclopentyl methyl ether용매

실험 절차

To a solution of 7-chloro-4-iodo-5-methyl-1-tosyl-1H-indole (98 mg, 0.220 mmol) and DMF (34 μL, 0.440 mmol) in cyclopentyl methyl ether (2 mL) at −78° C., was added n-butyllithium (2.5 M in hexanes, 114 μL, 0.286 mmol). After 80 minutes additional n-butyllithium (2.5 M in hexanes, 0.11 mL, 0.286 mmol) was added. After 15 more minutes the reaction was quenched with MeOH (0.5 mL) and sat. aq. NH4Cl. The layers were separated and the aqueous layer was extracted with EtOAc, washed with brine, dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 347.9 (M+H).

후처리

  1. customAfter 15 more minutes the reaction was quenched with MeOH (0.5 mL) and sat. aq. NH4Cl
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes)

출처 및 근거

ORD 기록
ord-f2214282ced7411fb3572f6b48f2e8c1
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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