Water → HCID 59557276, compound

HRID 1173523Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=3.[C:18]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].O>CN(C=O)C.C(OCC)(=O)C>[C:18]([C:22]1[CH:23]=[CH:24][C:25]([CH2:26][N:8]2[C:7]3[CH:6]=[CH:5][C:4]([Br:3])=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[C:12]([Br:17])[CH:13]=3)=[CH:28][CH:29]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 60 °C

Procedure

In a 250 ml one-neck flask provided with a reflux condenser, 990 mg (41.2 mmol) of NaH were suspended in 80 ml of dry DMF under protective gas. 10 g (30.8 mmol) of 3,6-dibromocarbazole in 80 ml of DMF were added dropwise to this reaction mixture at RT over a period of 20 minutes. A solution of 4-(tert-butyl)-benzyl bromide in 50 ml of DMF was subsequently added dropwise and the mixture was heated at 60° C. for 8 hours. After cooling to room temperature, 300 ml of water and 200 ml of ethyl acetate were carefully added. The organic phase was washed with 4×50 ml of H2O, then dried over MgSO4 and the solvents were removed under reduced pressure. The pure product was obtained by recrystallization from n-hexane. Yield: 11 g (78%); HPLC purity: 99.4%.

Workup

customIn a 250 ml one-neck flask provided with a reflux condenser
temperatureAfter cooling to room temperature
washThe organic phase was washed with 4×50 ml of H2O
dry with materialdried over MgSO4
customthe solvents were removed under reduced pressure
customThe pure product was obtained by recrystallization from n-hexane

Sources & evidence

ORD record: ord-bd946f7de27e450686f890bfb8a3079f
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834136B2

Reaction notes

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