Water → HCID 22031800, compound

HRID 1792583Notes

Reaction equation

HRID 1792583 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[C:17]([C:40]4[CH:50]=[CH:49][C:43]([C:44](OCC)=[O:45])=[CH:42][CH:41]=4)=[N:18][N:19]([C:21]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[F-].[Na+]>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[C:17]([C:40]4[CH:50]=[CH:49][C:43]([CH2:44][OH:45])=[CH:42][CH:41]=4)=[N:18][N:19]([C:21]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 5235Sodium FluorideHCID 21226445Aluminium lithium hydrideHCID 22031836HCID 22031836, compound

Product 1

HCID 22031800HCID 22031800, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

2 g 6-bromo-3-(2-pyridyl)imidazo[1,2-a]pyridine (compound in Production Example 63) and 5 g mixture of methyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]benzoate and ethyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]benzoate were reacted in the same manner as in Example 10, whereby 4.54 g mixture of methyl 4-[4-(3-pyridin-2-ylimidazo[1,2-a]pyridin-6-yl)-1-trityl-1H-pyrazol-3-yl]-benzoate and ethyl 4-[4-(3-pyridin-2-ylimidazo[1,2-a]-pyridin-6-yl)-1-trityl-1H-pyrazol-3-yl]benzoate was obtained as a pale yellow amorphous. 638 mg of this ester mixture was added to 10 mL suspension of 50 mg lithium aluminum hydride in tetrahydrofuran, and the mixture was stirred at 50° C. for 2 hours. The reaction solution was cooled on iced water, then 220 mg sodium fluoride and 80 μL water were added thereto, and the reaction solution was returned to room temperature and stirred for 40 minutes. Insolubles were filtered off, and the filtrate was evaporated. The residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 298 mg of the title compound as white crystals.

Workup

  1. customwas returned to room temperature
  2. stirringstirred for 40 minutes
  3. filtrationInsolubles were filtered off
  4. customthe filtrate was evaporated
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ddfccf8ab1374fd687a6ff99a69c6290
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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