Cesium carbonate → HCID 58961601, compound

HRID 916972Notes

Reaction equation

Cl[C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:7]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[CH:6][C:3]=1[C:4]#[N:5].[F:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]([OH:34])[CH3:33])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[C:8]1[C:7]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[CH:6][C:3]([C:4]#[N:5])=[C:2]([O:34][CH:32]([C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=2)[CH3:33])[N:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To an oven-dried round bottom flask was added toluene (1 mL), the product of Step D of Example 114 (0.050 g; 0.134 mmol); 1-(4-flourophenyl)ethanol (0.070 mL; 0.536 mmol), and cesium carbonate (0.218 g; 0.670 mmol). The reaction mixture was heated at 100° C. and stirred for 16 hours. The reaction mixture was allowed to cool to room temperature, then it was partitioned between ethyl acetate and 2N aq. NaOH solution. The organic portion was separated and washed with more 2N aq. NaOH solution (2×), brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification was done by MPLC (silica gel; 0-10% ethyl acetate:hexane) to afford 0.051 g of the desired product: m/e=355 (M-1-(4-flourophenyl)ethyl group) Rt=4.9 min on LCMS.

Workup

temperatureto cool to room temperature
customit was partitioned between ethyl acetate and 2N aq. NaOH solution
customThe organic portion was separated
washwashed with more 2N aq. NaOH solution (2×), brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification

Sources & evidence

ORD record: ord-02f8ae71dad94f5fb4cbe3ef9c8fed5e
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271266B2

Reaction notes

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