Cyanogen Bromide → HCID 15684562, compound

HRID 728149Notes

Reaction equation

HRID 728149 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]3[CH:17]=[C:16]([O:18][CH2:19][CH3:20])[CH:15]=[CH:14][N:13]3[C:21]=2[CH3:22])=[CH:4][C:3]=1[OH:23].[N:24]#[C:25]Br>C(O)C>[CH2:19]([O:18][C:16]1[CH:15]=[CH:14][N:13]2[C:21]([CH3:22])=[C:10]([CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]4[N:1]=[C:25]([NH2:24])[O:23][C:3]=4[CH:4]=3)[N:11]=[C:12]2[CH:17]=1)[CH3:20]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 15684647HCID 15684647, compound

Product 1

HCID 15684562HCID 15684562, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-[2-(4amino-3-hydroxyphenyl)ethyl]-7-ethoxy-3-methylimidazo[1,2-a]pyridine (1.6 g) and cyanogen bromide (0.7 g) in ethanol (24 ml) was stirred for 1.5 hours at ambient temperature. The solvent was evaporated in vacuo. To the residue was added a mixture of tetrahydrofuran, ethyl acetate and water, and the mixture was adjusted to pH 8 with 20% aqueous potassium carbonate solution. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated and the residue was triturated with a solution of diethyl ether and ethyl acetate and precipitate was collected by filtration to give 6-[2-(7-ethoxy-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]-2-aminobenzoxazole (1.12 g).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionTo the residue was added
  3. additiona mixture of tetrahydrofuran, ethyl acetate and water
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was triturated with a solution of diethyl ether and ethyl acetate and precipitate
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-a61d16e586554fbaac891c58b741050f
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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