3-(Chloromethyl)pyridine hydrochloride → 2-(3-methoxyphenyl)-6-phenyl-1-(3-pyridylmethyl)-1H-imidazo[4,5-b]pyridine

HRID 1437474Notes

Reaction equation

HRID 1437474 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(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C.Cl.[N:44]1[CH:49]=[CH:48][CH:47]=[C:46]([CH2:50]Cl)[CH:45]=1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]([CH2:50][C:46]3[CH:45]=[N:44][CH:49]=[CH:48][CH:47]=3)[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 233943-(Chloromethyl)pyridine hydrochlorideHCID 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 230255782-(3-methoxyphenyl)-6-phenyl-1-(3-pyridylmethyl)-1H-imidazo[4,5-b]pyridineYield 65%

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) (80 mg), 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine resin (PS-BEMP, 2.2 mmol/g) (326 mg) and N,N-dimethyl formamide (4.5 ml) was shaken at room temperature for 1 hour. To the mixture was added 3-pyridylmethylchloride hydrochloride (52 mg), and the mixture was further shaken at room temperature for 15 hours. Purification was carried out in a manner similar to Example 222 to obtain 2-(3-methoxyphenyl)-6-phenyl-1-(3-pyridylmethyl)-1H-imidazo[4,5-b]pyridine (67 mg, 65%).

Workup

  1. stirringthe mixture was further shaken at room temperature for 15 hours
  2. customPurification

Sources & evidence

ORD record
ord-c699416916e14a65994003607c63060e
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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