Ethyl Acetate → HCID 59199268, compound

HRID 2079692Notes

Reaction equation

HRID 2079692 reaction equation
[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:19]Br.C(OCC)(=O)C>C(O)(=O)C>[BrH:19].[Br:19][C:12]1[CH:13]=[C:14]([C:15]([F:18])([F:16])[F:17])[C:9]([NH:8][CH2:7][CH2:6][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:10][CH:11]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 55023198N-(2-(pyrrolidin-1-yl)ethyl)-3-(trifluoromethyl)pyridin-2-amine

Product 2

HCID 260Hydrogen BromideHCID 59199268HCID 59199268, compoundYield 142.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To the solution of N-(2-(pyrrolidin-1-yl)ethyl)-3-(trifluoromethyl)pyridin-2-amine (1030 mg, 4 mmole) in 10 ml of acetic acid, bromine (203 ul, 4 mmole) was added. The reaction solution was stirred at room temperature for 1.5 hr and then concentrated under vacuo to give an orange solid. The crude product was dissolved with 40 ml of ethyl acetate to give a yellow milky mixture that was then filtered and washed to give an ivory powder as HBr salt of 5-bromo-N-(2-(pyrrolidin-1-yl)ethyl)-3-(trifluoromethyl)pyridin-2-amine (963 mg). ES/MS m/z 335.9, 337.9 (MH+).

Workup

  1. concentrationconcentrated under vacuo
  2. customto give an orange solid
  3. customto give a yellow milky mixture that
  4. filtrationwas then filtered
  5. washwashed

Sources & evidence

ORD record
ord-64c3ba97e3bf47d5a70b1375fb900a6e
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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