Sodium Hydroxide → HCID 23025599, compound

HRID 1437459Notes

Reaction equation

HRID 1437459 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19](Cl)=O)=[CH:14][CH:13]=1.C(OCC)(=O)C.O1CCCC1.[OH-].[Na+]>O>[Br:9][C:5]1[CH:6]=[C:7]2[NH:8][C:19]([CH2:18][C:15]3[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=3)=[N:1][C:2]2=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 6911565-Bromopyridine-2,3-diamineHCID 27346884-Methoxyphenylacetyl chlorideHCID 21939870Tetrahydrofuran ethyl acetate

Product 1

HCID 23025599HCID 23025599, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
170 °C

Procedure

A mixture of 2,3-diamino-5-bromopyridine (Compound of Reference Example 1) (1.32 g) and 4-methoxyphenylacetyl chloride (1.29 g) was stirred in the absence of solvent at 170° C. for 1.5 hour. The mixture was distributed with ethyl acetate-tetrahydrofuran (3:1, v/v) and water (at that time, the water layer was neutralized with 1 N sodium hydroxide). The organic layer was washed with water, dried over MgSO4, and the solvent was distilled off under reduced pressure. The resulting crystals were collected by filtration to obtain 6-bromo-2-(4-methoxybenzyl)-1H-imidazo[4,5-b]pyridine (1.22 g, 55%).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. distillationthe solvent was distilled off under reduced pressure
  4. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-abf5c7fe0b2c42d1bdd2cab5553f9a0d
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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