4-Bromoaniline → 3H-Imidazo[4,5-b]pyridine-6-carboxamide, N-(4-bromophenyl)-2-[(2,6-dichlorophenyl)amino]-5-methoxy-3-methyl-

HRID 2368660Notes

Reaction equation

HRID 2368660 reaction equation
C[Al](C)C.CCCCCC.[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[NH:27][C:28]1[N:42]([CH3:43])[C:31]2=[N:32][C:33]([O:40][CH3:41])=[C:34]([C:36](OC)=[O:37])[CH:35]=[C:30]2[N:29]=1>C1COCC1.O.C(O)(=O)C.CO>[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:36]([C:34]2[CH:35]=[C:30]3[N:29]=[C:28]([NH:27][C:21]4[C:22]([Cl:26])=[CH:23][CH:24]=[CH:25][C:20]=4[Cl:19])[N:42]([CH3:43])[C:31]3=[N:32][C:33]=2[O:40][CH3:41])=[O:37])=[CH:14][CH:13]=1

Participants

9

Reactant 4

HCID 78074-BromoanilineHCID 8058HexaneHCID 16682925TrimethylaluminumHCID 67379714HCID 67379714, compound

Product 1

HCID 451379893H-Imidazo[4,5-b]pyridine-6-carboxamide, N-(4-bromophenyl)-2-[(2,6-dichlorophenyl)amino]-5-methoxy-3-methyl-

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2 M trimethyl aluminium solution in hexane (0.35 mL, 0.35 mmol) was added to 4-bromo-aniline (50 mg, 0.31 mmol) in 3.0 mL THF and the mixture stirred at ambient temperature for 1 h. Then methyl 2-(2,6-dichlorophenylamino)-5-methoxy-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylate (0.10 g, 0.26 mmol) was added and the mixture stirred at 60° C. for 16 h. Then methanol and acetic acid were added, the mixture poured into water. The precipitate was filtered off, washed with water and dried. Then the product was purified by preparative HPLC (RP Symmetry C18, 8 μm; eluent gradient: (water+0.15% formic acid)/acetonitrile=85:15→0:100).

Workup

  1. stirringthe mixture stirred at 60° C. for 16 h
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried
  5. customThen the product was purified by preparative HPLC (RP Symmetry C18, 8 μm; eluent gradient: (water+0.15% formic acid)/acetonitrile=85:15→0:100)

Sources & evidence

ORD record
ord-02ffda75c1904177a639ae86e95ef48d
Source dataset
uspto-grants-2014_04
Patent number
US08703796B2

Reaction notes

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