HCID 69270136, compound → HCID 69269366, compound

HRID 751531Notes

Reaction equation

[C:1]([O:5][C:6](=[O:31])[N:7]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[N:16]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)[CH2:15][CH2:14]2)([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6](=[O:31])[N:7]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[N:16]([C:18]1[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=1)[CH:15]=[CH:14]2)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 90 °C

Procedure

Add active manganese dioxide (0.8 g, 9.0 mmol) to a solution of benzyl-[1-(pyridin-4-yl)-2,3-dihydro-1H-indol-7-ylmethyl]carbamic acid tert-butyl ester (0.39 mg, 0.94 mmol) in toluene. Stir the mixture at 90° C. for 16 hours. Cool and filter, then concentrate the filtrate. Purify by chromatography (silica gel; hexane/ethyl acetate; 3:1 to 0:1) to isolate a solid as the title compound (200 mg, 50%). MS (ESI) m/z 414 (M+H)+.

Workup

temperatureCool
filtrationfilter
concentrationconcentrate the filtrate
customPurify by chromatography (silica gel; hexane/ethyl acetate; 3:1 to 0:1)

Sources & evidence

ORD record: ord-2911f1dc223e40acb8cf7a4b85736b75
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405305B2

Reaction notes

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