Diisobutylaluminum hydride → HCID 25174777, compound

HRID 1097306Notes

Reaction equation

HRID 1097306 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[N:15][N:14]3[C:17]([C:20]4[CH:25]=[CH:24][N:23]=[C:22]([C:26]5[CH:30]=[CH:29][O:28][CH:27]=5)[CH:21]=4)=[CH:18][N:19]=[C:13]3[CH:12]=2)[CH:6]=1)C.CC(C[AlH]CC(C)C)C>C(Cl)Cl.C([O-])(O)=O.[Na+].CCOC(C)=O>[O:28]1[CH:29]=[CH:30][C:26]([C:22]2[CH:21]=[C:20]([C:17]3[N:14]4[N:15]=[CH:16][C:11]([C:7]5[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[CH:9][CH:8]=5)=[CH:12][C:13]4=[N:19][CH:18]=3)[CH:25]=[CH:24][N:23]=2)=[CH:27]1

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 25176544HCID 25176544, compound

Product 1

HCID 25174777HCID 25174777, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 86584982Sodium bicarbonate ethyl acetateSolvent

Conditions

Temperature
-70 °C

Procedure

3-[3-(2-Furan-3-yl-pyridin-4-yl)-imidazo[1,2-b]pyridazin-7-yl]-benzoic acid ethyl ester (Ex. 41) (1 eq, 0.122 mmol, 50 mg) is dissolved in DCM (1 ml) and the reaction mixture is cooled to −70° C. DIBAL-H (1.5 M in THF, 10 eq, 1.22 mmol, 1.74 ml) is then added and the reaction is stirred at this temperature for 3 h. The reaction mixture is then poured in NaHCO3/EtOAc. The organic phase is separated and the aqueous phase is extracted with EtOAc. The combined organic phases are washed with brine, dried over MgSO4, filtered and the solvent is removed in vacuo. The reaction mixture is purified by flash column chromatography eluting with 9:1 DCM/MeOH to afford {3-[3-(2-Furan-3-yl-pyridin-4-yl)-imidazo[1,2-b]pyridazin-7-yl]-phenyl}-methanol as a light brown solid; [M+H]+=369

Workup

  1. customThe organic phase is separated
  2. extractionthe aqueous phase is extracted with EtOAc
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe reaction mixture is purified by flash column chromatography
  8. washeluting with 9:1 DCM/MeOH

Sources & evidence

ORD record
ord-cca65224cc49420c88c169db4c865ead
Source dataset
uspto-grants-2012_03
Patent number
US08143253B2

Reaction notes

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