Diisobutylaluminum hydride → (5-bromo-1-methyl-1H-indol-2-yl)methanol
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12](OCC)=[O:13])=[CH:5]2.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][OH:13])=[CH:5]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of ethyl 5-bromo-1-methyl-1H-indole-2-carboxylate (ca. 9.0 g) in CH2Cl2 (80 mL) was added DIBAL-H (1.0M in hexanes, 70.0 mL, 2.2 eq) at −78° C. over 15 min. The reaction was monitored by LC-MS. After stirring for 1 h at −78° C., the reaction was quenched with 1N HCl (20 mL) at −78° C. then allowed to warm to room temperature and stirred for additional 30 min to break aluminum emulsion. The biphasic mixture was extracted by ether/EtOAc (1:1, 3×50 mL). The combined organic layers were dried over Na2SO4 then concentrated to give (5-bromo-1-methyl-1H-indol-2-yl)methanol (ca. 7.8 g, quant.) which was used in the next step without further purification.
Workup
- customthe reaction was quenched with 1N HCl (20 mL) at −78° C.
- temperatureto warm to room temperature
- stirringstirred for additional 30 min
- extractionThe biphasic mixture was extracted by ether/EtOAc (1:1, 3×50 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationthen concentrated
Sources & evidence
- ORD record
- ord-2ffebfe3f7f6488f9b3cff203b4aeea9
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409905B2
Reaction notes
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