Methyl iodide → HCID 86701779, 화합물

HRID 2174133노트

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HRID 2174133 반응식
[C:1]([CH2:3][C:4]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH3:15])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])#[N:2].CI.[CH3:25][Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[C:1]([CH:3]([C:4]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH3:15])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:25])#[N:2]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 86701770HCID 86701770, 화합물

생성물 1

HCID 86701779HCID 86701779, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

tert-Butyl 4-(cyanomethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 155-B) (1.2 g, 4.00 mmol) was dissolved in THF (40.0 ml), MeI (0.300 ml, 4.79 mmol) was then added at −78° C. At this point, lithium bis(trimethylsilyl)amide (4.39 ml, 4.39 mmol) was added and the reaction stirred for 10 minutes. The reaction was then quenched at −78° C. with a saturated aq. solution of ammonium chloride, diluted with water and EtOAc and the layers were separated. The organic layer was dried over Na2SO4 and concentrated and purified via FCC (0-50% EtOAc:heptanes) to obtain the title compound. MS (ESI+) m/z 313.5 (M−H).

후처리

  1. customThe reaction was then quenched at −78° C. with a saturated aq. solution of ammonium chloride
  2. additiondiluted with water and EtOAc
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified via FCC (0-50% EtOAc:heptanes)

출처 및 근거

ORD 기록
ord-a4db3995feb54c998771a7a3f31a087c
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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