Allyl bromide → HCID 86701780, compound

HRID 2174134Notes

Reaction equation

HRID 2174134 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 86701780HCID 86701780, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-83a4eaed804a43c9820406c35ded5fa9
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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