Diisobutylaluminum hydride → 2-(6-fluoro-5-nitro-1H-indol-2-yl)-2-methylpropan-1-ol

HRID 1964473Notes

Reaction equation

HRID 1964473 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([CH3:23])([CH3:22])[C:12](OCC3C=CC=CC=3)=[O:13])[NH:8]2)=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([CH3:23])([CH3:22])[CH2:12][OH:13])[NH:8]2)=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 59129199Benzyl 2-(6-fluoro-5-nitro-1H-indol-2-yl)-2-methylpropanoate

Product 1

HCID 591293832-(6-fluoro-5-nitro-1H-indol-2-yl)-2-methylpropan-1-olYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 2-(6-fluoro-5-nitro-1H-indol-2-yl)-2-methylpropanoate (18.0 g, 0.05 mol) in CH2Cl2 (100 mL) was added DIBAL-H (12 mL) at −78° C. The mixture was stirred for 1 h at that temperature and was warmed to room temperature. The reaction was quenched with water and the aqueous layer was extracted with EtOAc (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4, the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel (10% EtOAc in petroleum ether) to give 2-(6-fluoro-5-nitro-1H-indol-2-yl)-2-methylpropan-1-ol (10.0 g, 77%). 1H NMR (300 MHz, CDCl3) 9.37 (s, 1 H), 8.32 (d, J=7.2 Hz, 1 H), 7.11 (d, J=11.7 Hz, 1 H), 6.36 (s, 1 H), 3.73 (d, J=5.1 Hz 2 H), 1.97 (t, J=5.1 Hz, 1 H), 1.39 (s, 6 H).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe aqueous layer was extracted with EtOAc (100 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel (10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-3e0744a1933245d8b15fa65924a5bc04
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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