Diisobutylaluminumhydride → HCID 178519463, compound

HRID 2182364Notes

Reaction equation

HRID 2182364 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[NH:14][C:13]3[CH:15]=[CH:16][C:17]([C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:20])=[CH:18][C:12]=3[N:11]=2)=[N:2]1.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[NH:14][C:13]3[CH:15]=[CH:16][C:17]([CH:19]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[OH:20])=[CH:18][C:12]=3[N:11]=2)=[N:2]1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 178519462HCID 178519462, compound

Product 1

HCID 178519463HCID 178519463, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of [2-(indazol-3-yl)-1H-benzoimidazol-5-yl]-phenyl-methanone [200 mg, Example 234(c)] in tetrahydrofuran (10 mL), at −78° C. and under an atmosphere of nitrogen, was treated dropwise with a solution of diisobutylaluminium hydride in tetrahydrofuran (1.18 mL, 1N). The reaction mixture was warmed to ambient temperature, then stirred for 16 hours and then partitioned between ether and sodium hydroxide solution (2N). The organic phase was washed with water, then with brine, then dried over magnesium sulfate and then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (3:1, v/v) to give [2-(indazol-3-yl)-1H-benzoimidazol-5-yl]-phenyl-methanol (161 mg) as a white solid. LC-MS (Method D): RT=21.89 minutes, 341.3 (M+H)+.

Workup

  1. custompartitioned between ether and sodium hydroxide solution (2N)
  2. washThe organic phase was washed with water
  3. dry with materialwith brine, then dried over magnesium sulfate
  4. customevaporated
  5. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (3:1

Sources & evidence

ORD record
ord-95d13b34da564ae8bd7fe0d2eb5923e5
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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