Diisobutylaluminum hydride → (3-iodo-1-methyl-1H-indazol-5-yl)methanol
Reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[N:9]=[C:8]2[I:15])=O.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[I:15][C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[C:5]([CH2:3][OH:2])[CH:6]=2)[N:10]([CH3:14])[N:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-iodo-1-methyl-1H-indazole-5-carboxylic acid methyl ester (0.95 g, 3.01 mmol) in CH2Cl2 (30 mL) at 0° C. was slowly added DIBAL-H (1.18 mL, 6.61 mmol). The reaction mixture was stirred at 0° C. for 1.5 h. Carefully quenched with MeOH (1 mL) then diluted with CH2Cl2 (20 mL) and added saturated aqueous Na+K+ tartrate (30 mL). The biphasic mixture was stirred vigorously at room temp for 1 h. The layers were separated and the aqueous phase was extracted with CH2Cl2. The combined organics were washed with water then dried over MgSO4 and concentrated to afford 810 mg of (3-iodo-1-methyl-1H-indazol-5-yl)methanol as a yellow waxy solid.
Workup
- customat 0° C.
- customCarefully quenched with MeOH (1 mL)
- additionthen diluted with CH2Cl2 (20 mL)
- additionadded saturated aqueous Na+K+ tartrate (30 mL)
- stirringThe biphasic mixture was stirred vigorously at room temp for 1 h
- customThe layers were separated
- extractionthe aqueous phase was extracted with CH2Cl2
- washThe combined organics were washed with water
- dry with materialthen dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2bc6f15d51aa4840af5cc95f4a7e8df8
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
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