Methyl iodide → HCID 86701779, compound

HRID 2174133Notes

Reaction equation

HRID 2174133 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 86701779HCID 86701779, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a4db3995feb54c998771a7a3f31a087c
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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