Allyl bromide → HCID 86701780, 화합물

HRID 2174134노트

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HRID 2174134 반응식
[C:1]([CH:3]([C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([CH3:16])=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:4])#[N:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:34](Br)[CH:35]=[CH2:36]>C1COCC1>[C:1]([C:3]([C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([CH3:16])=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])([CH2:36][CH:35]=[CH2:34])[CH3:4])#[N:2]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 86701779HCID 86701779, 화합물

생성물 1

HCID 86701780HCID 86701780, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To (±)-tert-butyl 4-(1-cyanoethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 156-A) (0.82 g, 2.61 mmol) in THF (13.04 ml) at −78° C. was added LiHMDS (1M in hexane, 3.13 ml, 3.13 mmol) and stirred for 7 minutes. At this point, allyl bromide (0.563 ml, 6.52 mmol) was added and the reaction stirred for 2 hours at −78° C. Reaction was then quenched with a saturated solution of aq. ammonium chloride and diluted with DCM. The layers were separated and the organic layer was dried over Na2SO4 and concentrated to an oil that was absorbed onto silica and purified via FCC (0-30% EtOAc:heptanes) to give the title compound. MS (ESI+) m/z 355.4 (M+H).

후처리

  1. stirringthe reaction stirred for 2 hours at −78° C
  2. customReaction
  3. customwas then quenched with a saturated solution of aq. ammonium chloride
  4. additiondiluted with DCM
  5. customThe layers were separated
  6. dry with materialthe organic layer was dried over Na2SO4
  7. concentrationconcentrated to an oil that
  8. customwas absorbed onto silica
  9. custompurified via FCC (0-30% EtOAc:heptanes)

출처 및 근거

ORD 기록
ord-83a4eaed804a43c9820406c35ded5fa9
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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