Hydrochloric Acid → HCID 178517704, compound

HRID 383274Notes

Reaction equation

HRID 383274 reaction equation
C[O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]3[C:15]([C:18]4[CH:23]=[CH:22][N:21]=[C:20]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH:19]=4)=[CH:16][N:17]=[C:11]3[CH:10]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.Cl.O.[OH-].[Na+]>CCO>[C:24]1([C:20]2[CH:19]=[C:18]([C:15]3[N:12]4[CH:13]=[CH:14][C:9]([C:8]5[C:3]([OH:2])=[N:4][CH:5]=[CH:6][CH:7]=5)=[CH:10][C:11]4=[N:17][CH:16]=3)[CH:23]=[CH:22][N:21]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68484571HCID 68484571, compound

Product 1

HCID 178517704HCID 178517704, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-(2-Methoxy-pyridin-3-yl)-3-(2-phenyl-pyridin-4-y1)-imidazo[1,2-a]pyridine (Ex. 1.100) (1 eq, 0.38 mmol, 145 mg) is dissolved in EtOH (0.5 ml) and HCl (37% in H2O, 0.04 eq, 0.015 mmol, 0.5 ml) is added. The reaction is heated at reflux for 3 h and is cooled down to rt before H2O is added. The pH is adjusted to 7 with the addition of NaOH (4N) and the suspension is filtered. The solid is washed with a mixture H2O/EtOH 4:1 and dried in vacuo to afford 3-[3-(2-Phenyl-pyridin-4-yl)-imidazo[1,2-a]pyridin-7-yl]-pyridin-2-ol as a light yellow oil; [M+H]+=365

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux for 3 h
  3. additionis added
  4. filtrationthe suspension is filtered
  5. washThe solid is washed with a mixture H2O/EtOH 4:1
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4a0e1e6ecb3b47e395d6abd2ac59704a
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

Loading…