Methyl iodide → HCID 23654624, compound

HRID 597960Notes

Reaction equation

HRID 597960 reaction equation
[Br:1][C:2]1[C:13]([O:14][CH3:15])=[N:12][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH:10]([CH3:11])[C:4]=2[C:3]=1[Br:16].CI.[C:19]([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[Br:1][C:2]1[C:13]([O:14][CH3:15])=[N:12][C:5]2[CH2:6][CH2:7][N:8]([CH3:19])[CH2:9][CH:10]([CH3:11])[C:4]=2[C:3]=1[Br:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 23653912HCID 23653912, compound

Product 1

HCID 23654624HCID 23654624, compoundYield 561.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,4-dibromo-2-methoxy-5-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine (32.5 mg, 9.30 μmol), MeI (5.8 μl, 93.0 μmol), Na2CO3 (19.7 mg, 18.3 μmol) and DMF (5 ml) was stirred for 3 d at room temperature. The reaction was quenched with sat. aq. NaHCO3 and extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated in vacuo and purified by column chromatography to give 19.0 mg (56%) of 3,4-dibromo-2-methoxy-5,7-dimethyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine. 1H-NMR (CDCl3) δ 3.89 (s, 3H), 3.63 (m, 1H), 3.25 (m, 1H), 2.88 (m, 3H), 2.30 (s, 3H), 2.28 (dd, 1H), 2.14 (m, 1H), 1.26 (d, 3H) ppm.

Workup

  1. customThe reaction was quenched with sat. aq. NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-22fe8f041ab74640b18080e9b128ba21
Source dataset
uspto-grants-2011_03
Patent number
US07897595B2

Reaction notes

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