Acetic Acid → HCID 25260942, compound

HRID 383279Notes

Reaction equation

HRID 383279 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([C:22]5[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=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.C(Cl)Cl>[CH:29]([N:25]1[CH2:24][CH:23]=[C: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)[CH2:27][CH2:26]1)([CH3:31])[CH3:28]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 252609473-(2-Phenyl-pyridin-4-yl)-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-imidazo[1,2-a]pyridine

Product 1

HCID 25260942HCID 25260942, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-Phenyl-pyridin-4-yl)-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-imidazo[1,2-a]pyridine (Ex. 1.190) (1.0 eq, 0.2 mmol, 90 mg) in MeOH (2 ml) is added acetone (10 eq, 1.04, 0.76 ml) and acetic acid (2 eq, 0.21 mmol, 0.1 ml) and the reaction mixture is stirred at room temperature for 30 min. After this time sodium triacetoxyborohydride (5 eq, 0.52 mmol, 116 mg) is added to the reaction mixture and is stirred for a further 2 h. The reaction is diluted with CH2Cl2 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-1,2,3,6-tetrahydro-pyridin-4-yl)-3-(2-phenyl-pyridin-4-yl)-imidazo[1,2-a]pyridine as a light yellow solid; [M+H]+=395

Workup

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

Sources & evidence

ORD record
ord-d7b9d1911e304173b5d78d2fb167342b
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

Loading…