Methyl iodide → HCID 58093447, compound

HRID 474987Notes

Reaction equation

HRID 474987 reaction equation
CI.[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:15]3[C:14](=[O:16])[CH2:13][CH2:12][CH2:11][C:10]=3[NH:9][C:8]=2[N:17]=1.[C:18]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:15]3[C:14](=[O:16])[CH2:13][CH2:12][CH2:11][C:10]=3[N:9]([CH3:18])[C:8]=2[N:17]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 58093335HCID 58093335, compound

Product 1

HCID 58093447HCID 58093447, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (0.45 mL, 7.1 mmol) was added to a solution of 2-bromo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indol-5-one (1.6 g, 5.9 mmol) and Cs2CO3 (2.3 g, mmol) in DMF (21 mL) under N2 and stirred for 3 h at ambient temperature. The mixture was quenched with H2O (30 mL), upon which a solid precipitated out of solution. The solids were collected by filtration and washed with H2O (100 mL) to provide the title compound (1.47 g, 88%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 8.18 (d, J=8.1 Hz, 1H), 7.43 (d, J=7.8 Hz, 1H), 3.74 (s, 3H), 3.03 (t, J=6.0 Hz, 2H), 2.50-2.44 (m, 2H, overlap with H2O peak), 2.20-2.12 (m, 2H).

Workup

  1. customThe mixture was quenched with H2O (30 mL), upon which a solid
  2. customprecipitated out of solution
  3. filtrationThe solids were collected by filtration
  4. washwashed with H2O (100 mL)

Sources & evidence

ORD record
ord-5fb29633345a41028f1abda293bf83b6
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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