Cesium carbonate → HCID 86087089, compound

HRID 1992919Notes

Reaction equation

HRID 1992919 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:6]([OH:14])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.F[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][CH2:3][C:4]1[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:6]([O:14][C:22]2[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 68537345HCID 68537345, compound

Product 1

HCID 86087089HCID 86087089, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[(Methyloxy)methyl]-2-phenyl-1-naphthalenol (145) (46 mg, 0.17 mmol) and 4-fluorobenzaldehyde was heated with Cs2CO3 in DMF at 100° C. to give 20 mg (30%) of the title compound (146) as a light yellow viscous oil. 1H NMR (400 MHz, CDCl3): δ 3.34 (s, 3H), 4.32 (s, 2H), 6.71 (d, J=8.8 Hz, 2H), 7.16-7.20 (m, 2H), 7.20-7.30 (m, 3H), 7.45 (t, J=7.5 Hz, 1H), 7.54 (t, J=7.4 Hz, 1H), 7.62 (d, J=8.6 Hz, 2H), 7.81 (d, J=8.4 Hz, 1H), 7.95 (d, J=9.0 Hz, 1H), 7.98 (s, 1H), 9.79 (s, 1H). LCMS (APCI): m/z 369 (M+H)+.

Sources & evidence

ORD record
ord-55618815909347d59ba124ae19cde1e5
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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