N-bromobutanimide → 7-Bromo-5-methyl-1-tosyl-1H-indol-4-amine

HRID 2174055Notes

Reaction equation

[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=[CH:5][C:4]=2[C:3]=1[NH2:21].C1C(=O)N([Br:29])C(=O)C1>CN(C=O)C>[Br:29][C:9]1[C:8]2[N:7]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=[CH:5][C:4]=2[C:3]([NH2:21])=[C:2]([CH3:1])[CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-methyl-1-tosyl-1H-indol-4-amine (Example 110-F) (1.06 g, 3.53 mmol) in DMF (35.3 mL) at 0° C. was added NBS (0.628 g, 3.53 mmol), and the mixture was stirred at 0° C. After 5 minutes the reaction was quenched with sat. aq. NaHCO3, then with sat. aq. sodium thiosulfate, extracted with EtOAc (2×), dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-80% EtOAc in heptanes) to provide the title compound, which was used in the next reaction without any further purification. MS (ESI+) m/z 379.0, 380.9 (M+H).

Workup

customAfter 5 minutes the reaction was quenched with sat. aq. NaHCO3
extractionwith sat. aq. sodium thiosulfate, extracted with EtOAc (2×)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe resulting residue was purified by flash chromatography (0-80% EtOAc in heptanes)

Sources & evidence

ORD record: ord-fb0dccd38a4a412e9b371ef4f26bdce0
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

Loading…