Borane;tetrahydrofuran → ethyl 7-bromo-3-(3-hydroxypropyl)-1H-indole-2-carboxylate

HRID 2095238Notes

Reaction equation

HRID 2095238 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][C:18](OCC)=[O:19].B.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][OH:19]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 68940416ethyl 7-bromo-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate

Product 1

HCID 68943187ethyl 7-bromo-3-(3-hydroxypropyl)-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of EXAMPLE 1A (1.85 g) in THF (50 mL) was added 1M borane•THF (30 mL). The mixture was stirred at room temperature for 16 hours, quenched with methanol (10 mL) and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5-25% ethyl acetate/hexanes.

Workup

  1. customquenched with methanol (10 mL)
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 5-25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-14134b3480c24089af02995c773fc263
Source dataset
uspto-grants-2013_05
Patent number
US08445679B2

Reaction notes

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