Morpholine → 6-Bromo-2-[4-(3-morpholin-4-ylpropoxy)phenyl]-3H-imidazo[4,5-b]pyridine

HRID 2218364Notes

Reaction equation

HRID 2218364 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20]Cl)=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[I-].[Li+].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CN(C=O)C.C(Cl)Cl.CO.N>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 66321Lithium iodideHCID 178478466HCID 178478466, compound

Product 1

HCID 1784194426-Bromo-2-[4-(3-morpholin-4-ylpropoxy)phenyl]-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584172Ammonia methanol dichloromethaneSolvent

Procedure

A solution of 6-bromo-2-[4-(3-chloropropoxy)phenyl]-3H-imidazo[4,5-b]pyridine (50 mg, 0.14 mmol), lithium iodide (20 mg, 0.15 mmol) and morpholine (0.1 ml, 1.15 mmol) in DMF (5 ml) was heated at 100° C. for 6 h. Column chromatography on silica using methylene chloride/methanol/ammonia as eluent afforded the title compound in almost quantitative yield.

Sources & evidence

ORD record
ord-781a4f5b4578488baf414060aa9f1686
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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