Hydrogen Bromide → 8-Fluoroimidazo(1,2-a)pyridine

HRID 2232435Notes

Reaction equation

HRID 2232435 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:10][CH:11]=O.C(OC(OCC)CBr)C.Br.C(=O)(O)[O-].[Na+]>O>[F:8][C:7]1[C:2]2[N:3]([CH:10]=[CH:11][N:1]=2)[CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 105131Acetaldehyde, bromo-HCID 516892Sodium BicarbonateHCID 27628092-Amino-3-fluoropyridine

Product 1

HCID 113095388-Fluoroimidazo(1,2-a)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-3-fluoropyridine (21.1 g) is added to a solution of bromoacetaldehyde prepared from 74 g of bromoacetaldehyde diethylacetal, 18.5 ml of aqueous hydrogen bromide solution and 18.5 ml of water and made to react in the presence of sodium bicarbonate in aqueous ethanolic solution giving 12 g of the above-identified compound, bp. 91°-100° C./1-1.5 mmHg, which solidifies at room temperature.

Sources & evidence

ORD record
ord-9dc79665f9f045c297ac41f7132703ea
Source dataset
uspto-grants-1988_11
Patent number
US04788185

Reaction notes

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