Tin dichloride dihydrate → 7,7-Dimethyl-5-pent-2-ynyl-2-phenethyl-5,7-dihydro-1H-imidazo [4.5-f]indol-6-one

HRID 2235403Notes

Reaction equation

[CH3:1][C:2]1([CH3:31])[C:10]2[C:5](=[CH:6][C:7]([N+:22]([O-])=O)=[C:8]([NH:11][C:12](=O)[CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=2)[N:4]([CH2:25][C:26]#[C:27][CH2:28][CH3:29])[C:3]1=[O:30].Cl[Sn]Cl.O>C1COCC1.Cl>[CH3:1][C:2]1([CH3:31])[C:10]2[CH:9]=[C:8]3[NH:11][C:12]([CH2:13][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[N:22][C:7]3=[CH:6][C:5]=2[N:4]([CH2:25][C:26]#[C:27][CH2:28][CH3:29])[C:3]1=[O:30]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of N-(3,3-dimethyl-6-nitro-2-oxo-1-pent-2-ynyl-2,3-dihydro-1H-indol-5-yl)-3-phenyl-propionamide (50 mg) in THF (0.5 ml) is added a solution of SnCl2.H2O (107 mg; 476 μmol) in hydrochloric acid (1 M; 2 ml) at RT. The mixture is stirred 2 h at RT and subsequent 2 h at 40° C. The reaction mixture is adjusted to pH 12 and extracted with CH2Cl2 (3×15 ml). The combined organic layer is dried over MgSO4 and concentrated in vacuo. The desired compound (19 mg) is obtained by flash chromatography on silica gel eluting with CH2Cl2/MeOH (99:1).

Workup

extractionextracted with CH2Cl2 (3×15 ml)
dry with materialThe combined organic layer is dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-195e2e323695461ca6611a4bcaa564b7
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714010B2

Reaction notes

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