Allyl bromide → HCID 86701780、化合物

HRID 2174134ノート

反応式

HRID 2174134 の反応式
[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]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 86701779HCID 86701779、化合物

生成物 1

HCID 86701780HCID 86701780、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-83a4eaed804a43c9820406c35ded5fa9
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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