Iodine → 1-Iodo-5-(5-carboxypentyl)-imidazo[1,5-a]pyridine

HRID 326123

Reaction equation

HRID 326123 reaction equation
[I:1]I.[C:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[N:16]2[CH:17]=[N:18][CH:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1)([OH:5])=[O:4].C(=O)(O)[O-].[Na+]>O.C(O)C>[I:1][C:19]1[N:18]=[CH:17][N:16]2[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:3]([OH:5])=[O:4])=[CH:12][CH:13]=[CH:14][C:15]=12

Participants

6

Reactant 3

HCID 807Iodine2×HCID 55390PirmagrelHCID 516892Sodium Bicarbonate

Product 1

HCID 132061571-Iodo-5-(5-carboxypentyl)-imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

Iodine crystals (1.9 g) are added to a well-stirred solution of 1.16 g of 5-(5-carboxypentyl)-imidazo[1,5-a]pyridine and 1.68 g of sodium bicarbonate in 10 ml of water and 1 ml of ethanol. Additional 4 ml of ethanol are added to dissolve the bulk of the iodine and stirring is continued for 45 minutes. The reaction mixture is diluted with 125 ml of water and extracted twice with methylene chloride at pH 8 (NaHCO3 added if necessary). The aqueous phase is concentrated in vacuo, charcoaled and adjusted to pH 4.5 with 2 N HCl. The precipitate is collected, dried and recrystallized from methanol/ether to give 1-iodo-5-(5-carboxypentyl)-imidazo[1,5-a]pyridine melting at 163°-165°.

Workup

  1. extractionextracted twice with methylene chloride at pH 8 (NaHCO3 added if necessary)
  2. concentrationThe aqueous phase is concentrated in vacuo
  3. customThe precipitate is collected
  4. customdried
  5. customrecrystallized from methanol/ether

Sources & evidence

ORD record
ord-ccb063dd798e465d93e4410aef082609
Source dataset
uspto-grants-1984_04
Patent number
US04444775

Linked notes

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