Water → Methyl 3-methyl-1-{3-(phenyl)propyl}-1H-indole-6-carboxylate
Reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.Br[CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+].O>CC(C)=O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:3]=1Participants
6
Procedure
A stirred solution of methyl 3-methyl-1H-indole-6-carboxylate (0.5 g, Reference Example 30) in acetone (35 ml) was treated with 1-bromo-3-phenylpropane (0.577 g) and sodium hydroxide (0.116 g). The mixture was stirred at room temperature for 12 hours then poured into water (35 ml) and then extracted three times with ethyl acetate (50 ml). The combined extracts were washed with dilute hydrochloric acid (50 ml, 1N) then with saturated sodium bicarbonate solution (50 ml), then dried over magnesium sulphate and then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (50:1, v/v) to yield the title compound (0.58 g).
Workup
- extractionextracted three times with ethyl acetate (50 ml)
- washThe combined extracts were washed with dilute hydrochloric acid (50 ml, 1N)
- dry with materialwith saturated sodium bicarbonate solution (50 ml), then dried over magnesium sulphate
- customevaporated
- additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (50:1
Sources & evidence
- ORD record
- ord-ae4ab98eba3f484ba184e862cd886cff
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07329675B2
Reaction notes
Loading…