Methyl iodide → HCID 86645397, compound

HRID 1944052Notes

Reaction equation

HRID 1944052 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]1[CH2:11][C:12](=[O:15])[CH2:13][CH2:14][C:8]1=[C:7]2[CH2:16][C:17]([O:19][CH2:20][CH2:21][CH3:22])=[O:18].[CH3:23][Si]([N-][Si](C)(C)C)(C)C.[Na+].CI>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]1[CH:11]([CH3:23])[C:12](=[O:15])[CH2:13][CH2:14][C:8]1=[C:7]2[CH2:16][C:17]([O:19][CH2:20][CH2:21][CH3:22])=[O:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 86645398HCID 86645398, compound

Product 1

HCID 86645397HCID 86645397, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of propyl (4-fluoro-7-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate in THF (0.17 M) was treated at −78° C. with a 1.0 M solution of NaHMDS in THF (1.2 eq.). After stirring for 10 min, MeI (2.0 eq.) was added. The cooling bath was removed and the mixture stirred for 1 hour, concentrated to dryness and the residue purified by chromatography on SiO2 (0-100% EtOAc/hexanes).

Workup

  1. customThe cooling bath was removed
  2. stirringthe mixture stirred for 1 hour
  3. concentrationconcentrated to dryness
  4. customthe residue purified by chromatography on SiO2 (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5a19aa1ebe9e4d98b33c02ba270af2b0
Source dataset
uspto-grants-2013_03
Patent number
US08394819B2

Reaction notes

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