Methyl iodide → (+/-)-tert-Butyl 4-(2-(5-cyanobenzo[d]oxazol-2-yl)-1-ethoxy-1-oxopropan-2-yl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174106노트

반응식

HRID 2174106 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([C:17]3[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22]4[C:18]=3[CH:19]=[CH:20][N:21]4[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:8][C:7]=2[CH:36]=1)#[N:2].[CH3:37]I.[H-].[Na+]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([C:17]3[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22]4[C:18]=3[CH:19]=[CH:20][N:21]4[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([CH3:37])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:8][C:7]=2[CH:36]=1)#[N:2]

참가 물질

5

반응물 3

HCID 6328Methyl iodide2회HCID 24758Sodium hydrideHCID 86701744(+/-)-tert-Butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-2-ethoxy-2-oxoethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

생성물 1

HCID 86701745(+/-)-tert-Butyl 4-(2-(5-cyanobenzo[d]oxazol-2-yl)-1-ethoxy-1-oxopropan-2-yl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (±)-tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-2-ethoxy-2-oxoethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 144-B) (139.5 mg, 0.285 mmol) in DMF (2.850 mL) were added successively MeI (0.080 mL, 1.282 mmol) and NaH (34.2 mg, 0.855 mmol) at 0° C. After stirring for 2.5 hrs at this temperature another additional aliquot of MeI (0.045 mL, 0.57 mmol) were added to the mixture. The mixture was allowed to stir at room temperature overnight. The reaction mixture was quenched with a saturated aq. solution of ammonium chloride at 0° C. and the layers were separated. The aqueous layer was extracted with AcOEt and the combined organic layers were concentrated to give crude product that was purified via FCC: Heptane/AcOEt:100/0 to 50/50 to obtain the title compound. MS (ESI+) m/z 504.38 (M+H).

후처리

  1. additionwere added to the mixture
  2. customThe reaction mixture was quenched with a saturated aq. solution of ammonium chloride at 0° C.
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with AcOEt
  5. concentrationthe combined organic layers were concentrated
  6. customto give crude product that
  7. customwas purified via FCC

출처 및 근거

ORD 기록
ord-6393a603d68b4314a9ef66358574a0a6
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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