Bromide ion → 1-(3,5-Di-tert-butyl-4-hydroxyphenyl)-2-[(pyridin-2-ylmethyl)amino]ethanone hydrobromide

HRID 249708

Reaction equation

HRID 249708 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C[Si](C)(C)N[Si](C)(C)C.[Li].[Br:19][CH2:20][C:21]([C:23]1[CH:28]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:26]([OH:33])=[C:25]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:24]=1)=[O:22].[Br-]>C1COCC1>[BrH:19].[C:29]([C:27]1[CH:28]=[C:23]([C:21](=[O:22])[CH2:20][NH:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)[CH:24]=[C:25]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:26]=1[OH:33])([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 4

HCID 259Bromide ionHCID 195092-PyridinemethanamineHCID 6161612-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-oneHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 866329581-(3,5-Di-tert-butyl-4-hydroxyphenyl)-2-[(pyridin-2-ylmethyl)amino]ethanone hydrobromideYield 48.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Aminomethyl)pyridine (100 mg) was initially introduced in absolute THF (12 ml) and treated with lithium hexamethyldisilazane solution (1.01 ml, 1 M in THF) at RT with stirring and under argon. After 30 min, 2-bromo-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone (0.5 eq., 151 mg, dissolved in 1.5 ml absolute THF) was added dropwise. For completion of the reaction, the remaining amount of bromide (151 mg) was added and after 2 hours the precipitate formed was filtered off with suction and dried. The 98 mg of the title compound obtained are contaminated with small amounts of THF which, however, do not interfere with the further reaction.

Workup

  1. customFor completion of the reaction
  2. customformed
  3. filtrationwas filtered off with suction
  4. customdried

Sources & evidence

ORD record
ord-95d0713d57cf489f97dd908458377bb5
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Linked notes

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