1,10-Phenanthroline → 4-(6-Benzylbenzo[d]oxazol-2-yl)-3-fluorobenzaldehyde

HRID 2075246Notes

Reaction equation

N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:21]([C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:45])[C:36]2[CH:41]=[CH:40][C:39]([CH:42]=[O:43])=[CH:38][C:37]=2[F:44])=[C:30](I)[CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1>[CH2:21]([C:28]1[CH:33]=[CH:32][C:31]2[N:34]=[C:35]([C:36]3[CH:41]=[CH:40][C:39]([CH:42]=[O:43])=[CH:38][C:37]=3[F:44])[O:45][C:30]=2[CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 90 °C

Procedure

1,10-Phenanthroline (0.016 g, 0.087 mmol), cuprous iodide (0.008 g, 0.044 mmol), cesium carbonate (0.21 g, 0.65 mmol), and N-(4-benzyl-2-iodophenyl)-2-fluoro-4-formylbenzamide (0.200 g, 0.44 mmol) were combined under argon. Dioxane (2 mL) was added and the reaction was sealed and heated to 90° C. for 24 h. The reaction was cooled and partitioned between EtOAc and water. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by ISCO, 40 g, 0-30% EtOAc/hexanes to give 4-(6-benzylbenzo[d]oxazol-2-yl)-3-fluorobenzaldehyde as a white solid. MS (ESI) m/z: Calculated: 331.1; Observed: 332.1 (M++1).

Workup

customthe reaction was sealed
temperatureThe reaction was cooled
custompartitioned between EtOAc and water
washThe organics were washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by ISCO, 40 g, 0-30% EtOAc/hexanes

Sources & evidence

ORD record: ord-1e28a09ac00148fd91dd9bcc38ff6797
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919519B2

Reaction notes

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