Dimethylformamide → HCID 86644569, compound

HRID 1891215Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([N:14]2[C:18]([C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])=[C:17]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:16]=[N:15]2)[CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42]Br)=[CH:40][CH:39]=1.CN(C=O)C>[Cl-].[Na+].O>[Br:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[N:13]=[C:12]([N:14]3[C:18]([C:19]([F:25])([F:24])[C:20]([F:23])([F:21])[F:22])=[C:17]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:16]=[N:15]3)[CH:11]=[CH:10][CH:9]=2)=[CH:40][CH:39]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To flask containing the title compound from Example 8 Step C (415 mg, 0.971 mmol) were added cesium carbonate (791 mg, 2.43 mmol), 4-bromobenzyl bromide (316 mg, 1.26 mmol), and DMF (6 mL), and the resulting mixture was stirred at 45° C. After 3 h, the reaction mixture was allowed to cool to room temperature, then was poured into brine and extracted with EtOAc. The organic phase was separated and concentrated in vacuo. Purification by chromatography on silica gel (0 to 25% EtOAc in hexanes, then 25 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 597.7 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.21 (s, 1H), 8.05 (d, J=8.0 Hz, 1H), 7.86 (t, J=8.0 Hz, 1H), 7.82 (dd, J=8.0, 2.0 Hz, 1H), 7.49-7.47 (m, 2H), 7.38-7.35 (m, 2H), 7.23 (d, J=8.5 Hz, 2H), 7.11-7.08 (m, 1H), 7.02 (d, J=8.5 Hz, 1H), 5.09 (s, 2H), 4.37 (q, J=7.0 Hz, 2H), 1.38 (t, J=7.0 Hz, 3H).

Workup

temperatureto cool to room temperature
extractionextracted with EtOAc
customThe organic phase was separated
concentrationconcentrated in vacuo
customPurification by chromatography on silica gel (0 to 25% EtOAc in hexanes

Sources & evidence

ORD record: ord-cb893e91bc44436eb126752290dcb146
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507512B2

Reaction notes

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