Diisobutylaluminumhydride → HCID 66765279, compound

HRID 1466785Notes

Reaction equation

HRID 1466785 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[N:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:12]=2[CH3:28])[CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH2:21]([N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:11]([S:10][C:6]2[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][CH:7]=2)=[C:12]1[CH3:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 21225700Diisobutylaluminumhydride2×HCID 66765006HCID 66765006, compound

Product 1

HCID 66765279HCID 66765279, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-(1-Benzyl-6-chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (1.08 g, 2.6 mmol) was dissolved in THF (20 mL) and the solution was cooled to −78° C. Diisobutylaluminum hydride (6.5 mL, 1.0M in THF, 6.5 mmol) was added dropwise and the reaction was stirred for 30 minutes then an additional amount of diisobutylaluminum hydride (6.5 mL, 1.0M in THF, 6.5 mmol) was added. The reaction was allowed to warm to 0° C. then quenched with H2O and HCl(aq.). The reaction was submitted to a standard workup procedure to give the title compound.

Workup

  1. temperatureto warm to 0° C.
  2. customthen quenched with H2O and HCl(aq.)

Sources & evidence

ORD record
ord-d266e245b964444cad769b39bbff21e5
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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