Acetic Acid → HCID 25260789, compound

HRID 383281Notes

Reaction equation

HRID 383281 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:28][C:29]([CH3:31])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH:29]([N:25]1[CH2:26][CH2:27][CH:22]([C:20]2[CH:19]=[CH:18][N:17]3[C:13]([C:11]4[CH:10]=[CH:9][N:8]=[C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[CH:12]=4)=[CH:14][N:15]=[C:16]3[CH:21]=2)[CH2:23][CH2:24]1)([CH3:31])[CH3:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 252609443-(2-Phenyl-pyridin-4-yl)-7-piperidin-4-yl-imidazo[1,2-a]pyridine

Product 1

HCID 25260789HCID 25260789, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(2-phenyl-pyridin-4-yl)-7-piperidin-4-yl-imidazo[1,2-a]pyridine (Ex. 1.198) (1.0 eq, 0.16 mmol, 80 mg) in MeOH (2 ml) is added acetone (10 eq, 1.6 mmol, 0.12 ml) and acetic acid (2 eq, 0.33 mmol, 0.19 ml) and the reaction mixture is stirred at room temperature for 30min. After this time sodium triacetoxyborohydride (5 eq, 0.82 mmol, 183 mg) is added to the reaction mixture and is stirred for a further 2 h. The reaction is diluted with CH2C12 and the organic phase is washed with NaHCO3. The aqueous layer is further extracted with EtOAc. The combined organic layers are washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo. The reaction mixture is purified by flash column chromatography eluting with 8:2 DCM/MeOH to yield 7-(1-Isopropyl-piperidin-4-yl)-3-(2-phenyl-pyridin-4-yl)-imidazo[1,2-a]pyridine as a light yellow solid; [M+H]+=397

Workup

  1. stirringis stirred for a further 2 h
  2. additionThe reaction is diluted with CH2C12
  3. washthe organic phase is washed with NaHCO3
  4. extractionThe aqueous layer is further extracted with EtOAc
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe reaction mixture is purified by flash column chromatography
  10. washeluting with 8:2 DCM/MeOH

Sources & evidence

ORD record
ord-565f0b4d529746a4a96b53baf3055f98
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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