Methyl iodide → 2-(3-methoxyphenyl)-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine

HRID 1437468Notes

Reaction equation

HRID 1437468 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[NH:10][C:11]3[C:12]([N:23]=2)=[N:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=3)[CH:6]=[CH:7][CH:8]=1.[B].[C:25](N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C.IC>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]([CH3:25])[C:11]3[C:12]([N:23]=2)=[N:13][CH:14]=[C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:16]=3)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine2×HCID 5462311BoronHCID 99483042-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridine

Product 1

HCID 230257402-(3-methoxyphenyl)-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridineYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridine (Compound of Example 1) (50 mg), 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine resin (PS-BEMP, 2.2 mmol/g) (113 mg) and N,N-dimethyl formamide (2 ml) was shaken at room temperature for 30 minutes. To the mixture was added iodomethane (28 mg), and the mixture was further shaken for 1 hour. After the resin was filtered off, the filtrate was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-chloroform-hexane (1:1:4 to 1:1:0, v/v) was concentrated under reduced pressure. The resulting crystals were collected by filtration to isolate 2-(3-methoxyphenyl)-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine (22 mg, 41%) (As a result of this reaction, a mixture of two isomers was obtained, and the isomer having higher polarity is the desired compound.)

Workup

  1. stirringthe mixture was further shaken for 1 hour
  2. filtrationAfter the resin was filtered off
  3. additionthe filtrate was poured into water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over MgSO4
  7. distillationthe solvent was distilled off under reduced pressure
  8. washthe fraction eluted with ethyl acetate-chloroform-hexane (1:1:4 to 1:1:0
  9. concentrationv/v) was concentrated under reduced pressure
  10. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-82755f29f3694717b033e7177f539fa1
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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