Water → 1-{2-[4-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}-2-methylpropan-2-ol

HRID 572182Notes

Reaction equation

HRID 572182 reaction equation
C[Mg]Br.[CH2:4]1COCC1.[N:9]1[CH:10]=[CH:11][N:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]3[CH:40]=[CH:39][C:24]([O:25][C:26]4[N:30]([CH2:31][C:32](=[O:34])[CH3:33])[C:29]5[CH:35]=[CH:36][CH:37]=[CH:38][C:28]=5[N:27]=4)=[CH:23][CH:22]=3)[C:13]=12.O>C1COCC1>[N:9]1[CH:10]=[CH:11][N:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]3[CH:22]=[CH:23][C:24]([O:25][C:26]4[N:30]([CH2:31][C:32]([CH3:4])([OH:34])[CH3:33])[C:29]5[CH:35]=[CH:36][CH:37]=[CH:38][C:28]=5[N:27]=4)=[CH:39][CH:40]=3)[C:13]=12

Participants

5

Reactant 3

HCID 962WaterHCID 867049891-{2-[4-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}propan-2-oneHCID 178420675HCID 178420675, compound

Product 1

HCID 683505881-{2-[4-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}-2-methylpropan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of cerium chloride(III) (296 mg) in THF (4 ml) was added dropwise 1 M methylmagnesium bromide-THF solution (1.2 ml) at −78° C. After stirring for 10 min, a solution of 1-{2-[4-(9H-imidazo[1′,2′:1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}propan-2-one (338 mg) obtained in Example 10 in THF (20 ml) was added dropwise at −78° C., and the obtained mixture was warmed to room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography (hexane/ethyl acetate), purified by HPLC (L-Column 2 ODS, 10 mM aqueous hydrogen carbonate ammonium-containing acetonitrile solution) and recrystallized from methanol/water to give the title compound (44.0 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. custompurified by HPLC (L-Column 2 ODS, 10 mM aqueous hydrogen carbonate ammonium-containing acetonitrile solution)
  6. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-989d4094304248b5a670ebde80fa6552
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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