Trimethylaluminum → tert-Butyl 2-(6-(8-chloro-4-methyl-1-oxopyrrolo[3,4-b]indol-2(1H,3H,4H)-yl)-1H-indol-1-yl)acetate

HRID 453857Notes

Reaction equation

[C:1]([O:5][C:6](=[O:34])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH:17][CH2:18][C:19]3[N:20]([CH3:33])[C:21]4[C:26]([C:27]=3[C:28]([O:30]C)=O)=[C:25]([Cl:32])[CH:24]=[CH:23][CH:22]=4)[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].[Al](C)(C)C>ClCCl.Cl>[Cl:32][C:25]1[C:26]2[C:27]3[C:28](=[O:30])[N:17]([C:14]4[CH:15]=[C:16]5[C:11]([CH:10]=[CH:9][N:8]5[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:34])=[CH:12][CH:13]=4)[CH2:18][C:19]=3[N:20]([CH3:33])[C:21]=2[CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Methyl 2-((1-(2-tert-butoxy-2-oxoethyl)-1H-indol-6-ylamino)methyl)-4-chloro-1-methyl-1H-indole-3-carboxylate (2.416 mmol, 1 equiv.) was dissolved in dichloromethane (36 ml), and (CH3)3Al (2 M solution in toluene, 4.83 mmol) was added at 0° C., under nitrogen. After 10 min, the reaction mixture was heated to 25° C. and then stirred for 2 h. The reaction mixture was diluted with dichloromethane and hydrolysed with 2 M HCl. The phases were separated, and the organic phase was washed with water and sat. NaCl solution (in each case 10 ml). Drying over Na2SO4 was then carried out, followed by concentration under reduced pressure. The product was crystallized from ethyl acetate. Yield: 89%

Workup

customThe phases were separated
washthe organic phase was washed with water and sat. NaCl solution (in each case 10 ml)
dry with materialDrying over Na2SO4
concentrationfollowed by concentration under reduced pressure
customThe product was crystallized from ethyl acetate

Sources & evidence

ORD record: ord-28c1b47fff0444c5bf8389b996d73246
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492559B2

Reaction notes

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