Hydrochloric Acid → [1-(4-methoxy-benzyl)-3-methyl-1H-indol-6-yl]-phenyl methanone

HRID 380407Notes

Reaction equation

CON(C)[C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH3:24])=[CH:11][N:12]2[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:8][CH:7]=1)=[O:5].[C:26]1([Mg]Cl)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl>O1CCCC1>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:12]2[C:13]3[C:9](=[CH:8][CH:7]=[C:6]([C:4]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:5])[CH:14]=3)[C:10]([CH3:24])=[CH:11]2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of N-methoxy-1-(4-methoxybenzyl)-3-methyl-N-methyl-1H-indole-6-carboxamide (2.215 g, Example 25) in tetrahydrofuran (55 ml) was treated with a solution of phenylmagnesium chloride in tetrahydrofuran (9.83 ml, 2M). The solution was stirred at 0° C. for 2 hours then poured into a mixture of ice and 1N hydrochloric acid (10 ml) and then partitioned between ethyl acetate (50 ml) and water (50 ml). The organic layer was dried over sodium sulphate then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2, v/v) to yield the title compound (2.05 g) as a yellow solid, m.p. 146-147° C. [Elemental analysis:—C,80.80; H,6.00; N,3.80%. Calculated for C24H21NO2:—C,81.10; H,5.96; N,3.94%].

Workup

custompartitioned between ethyl acetate (50 ml) and water (50 ml)
dry with materialThe organic layer was dried over sodium sulphate
customthen evaporated
additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2

Sources & evidence

ORD record: ord-8d5d43353a164b3b8ac7bf9b9a9f43aa
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303600B1

Reaction notes

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