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

HRID 576240Notes

Reaction equation

HRID 576240 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>[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 6331BoraneHCID 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 8028TetrahydrofuranSolvent2×

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-b8fb5e5297404142bfebb34bfd77fc8f
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

Loading…