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

HRID 2199711Notes

Reaction equation

HRID 2199711 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-d8f40d09dd134b89a18a83b7f5b2319b
Source dataset
uspto-grants-2016_06
Patent number
US09359296B2

Reaction notes

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