Cesium carbonate → HCID 59843028, compound

HRID 1878731Notes

Reaction equation

HRID 1878731 reaction equation
[F:1][C:2]1[C:7]([CH2:8][CH2:9][OH:10])=[CH:6][C:5]([C:11]2[S:12][CH:13]=[C:14]([CH3:16])[CH:15]=2)=[CH:4][N:3]=1.Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=2)[N:21]=[CH:20][CH:19]=1.C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([CH2:8][CH2:9][O:10][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=3)[N:21]=[CH:20][CH:19]=2)=[CH:6][C:5]([C:11]2[S:12][CH:13]=[C:14]([CH3:16])[CH:15]=2)=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 106078294-Chloro-7-methoxyquinolineHCID 59843096HCID 59843096, compound

Product 1

HCID 59843028HCID 59843028, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a 5 mL CEM microwave tube was added 2-(2-fluoro-5-(4-methylthiophen-2-yl)pyridin-3-yl)ethanol (0.06 g, 0.3 mmol), 4-chloro-7-methoxyquinoline (0.10 g, 0.5 mmol), racemic-2-(di-t-butylphosphino)-1,1′-binaphthyl (0.04 g, 0.1 mmol), palladium (II) acetate (0.02 g, 0.1 mmol), cesium carbonate (0.2 g, 0.5 mmol), and toluene (4 mL). The vial was sealed and heated at 80° C. in the closed system for 3 h. The reaction mixture was passed through the celite to separate the inorganic salt. Solvent was removed. The crude product was purified using SiO2 chromatography with CH2Cl2:MeOH (98%:2%) to afford the product as brown solid. MS (ESI pos. ion) m/z (MH+): 395.3. Calc'd exact mass for C22H19FN2O2S: 394.1. 1H NMR (300 MHz, Chloroform-d) δ ppm 2.30 (s, 3 H) 3.31 (t, J=6.21 Hz, 2 H) 3.94 (s, 3 H) 4.46 (t, J=6.21 Hz, 2 H) 6.65 (d, J=5.41 Hz, 1 H) 6.94 (s, 1 H) 7.07 (s, 1 H) 7.12 (dd, J=9.13, 2.56 Hz, 1 H) 7.36 (d, J=2.48 Hz, 1 H) 7.95 (dd, J=8.99, 2.41 Hz, 1 H) 8.05 (d, J=9.06 Hz, 1 H) 8.33 (s, 1 H) 8.67 (d, J=5.26 Hz, 1 H).

Workup

  1. customThe vial was sealed
  2. customto separate the inorganic salt
  3. customSolvent was removed
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-5112a8adbb8d421eb19faaaa3c91aaa6
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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