p-Fluoronitrobenzene → tert-butyl 7-(4-nitrophenoxy)-9H-carbazol-2-ylcarbamate

HRID 1879564Notes

Reaction equation

[OH:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:10][C:11]=3[NH:12]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].F[C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1>CN(C=O)C.O>[N+:36]([C:33]1[CH:34]=[CH:35][C:30]([O:1][C:2]2[CH:14]=[C:13]3[C:5]([C:6]4[CH:7]=[CH:8][C:9]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[CH:10][C:11]=4[NH:12]3)=[CH:4][CH:3]=2)=[CH:31][CH:32]=1)([O-:38])=[O:37]

Participants

Conditions

Temperature: 140 °C

Procedure

To a round bottom flask containing Compound 9 (80 mg, 0.268 mmol) in DMF (2 mL) was added potassium carbonate (74.1 mg, 0.536 mmol) and 4-fluoro-nitrobenzene (41.6 mg, 0.295 mmol). The reaction mixture was heated for 20 min at 140° C. After cooling down to rt, the mixture was diluted with water (20 mL) and extracted with EtOAc (20 mL×3). The organic layers were dried, concentrated. The residue was purified on a silica gel column (EtOAc: Hexanes=3:7) to afford Compound 10 as a yellow solid (50 mg, 0.12 mmol, 44% yield). 1H NMR (400 MHz, CDCl3) δ: 8.22 (d, J=9.2 Hz, 2H), 8.10 (br, 1H), 8.00-7.90 (m, 3H), 7.12 (s, 1H), 7.06-6.90 (m, 4H), 6.70 (br, 1H), 1.56 (s, 9H); LRMS for C23H21N3O5+H+, calc'd: 420.2. found: 420.2 (M+H+).

Workup

temperatureAfter cooling down to rt
extractionextracted with EtOAc (20 mL×3)
customThe organic layers were dried
concentrationconcentrated
customThe residue was purified on a silica gel column (EtOAc: Hexanes=3:7)

Sources & evidence

ORD record: ord-9a9ab4e540ae4d4c87e4668c2ec0dff2
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318132B2

Reaction notes

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