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Methyl iodide → N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-methoxypropyl)-3-methoxyaniline

HRID 404273
Notes
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Reaction equation

HRID 404273 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH2:18][CH:19]([OH:30])[CH2:20][NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)[C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=3.[CH3:31]I>CN(C=O)C.C(OCC)(=O)C>[Br:17][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:18][CH:19]([O:30][CH3:31])[CH2:20][NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)[C:7]3[C:15]([C:14]=2[CH:13]=1)=[CH:16][C:4]([Br:3])=[CH:5][CH:6]=3
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3103961P7C3-OMe

Product 1

HCID 46853449N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-methoxypropyl)-3-methoxyaniline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×
HCID 8857
Ethyl Acetate
Solvent

Procedure

Sodium hydride (9.0 mg, 0.23 mmol) was added to a stirring solution of 1-(3,6-dibromo-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol (99.3 mg, 0.20 mmol) in DMF 0.5 ml, 0.39 M). The solution was stirred at room temperature for about 70 minutes before the dropwise addition of a solution of methyl iodide (14 ml. 0.22 mol) in DMF (1.0 ml). The reaction was monitored by lc/ms for the consumption of SM and the appearance of O and N-methyl products. After 2.5 hours of stirring at r.t, conversion was about 30% and about 5% N-methyl product had formed. The reaction was stopped when an increase of N-Me to O-Me had been observed and conversion was about 50%. The brown solution was diluted with ethyl acetate and washed several times with water and finally brine. The organic layer was dried over Na2SO4, filtered and condensed. The mixture was purified by preparative TLC 30% EtOAc/hexanes.

Workup

  1. customlc/ms for the consumption of SM
  2. customabout 5% N-methyl product had formed
  3. temperaturean increase of N-Me to O-Me
  4. washwashed several times with water and finally brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customcondensed
  8. customThe mixture was purified by preparative TLC 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-192b25c420c545d0b127957cf1deb537
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748473B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes