Cesium carbonate → HCID 59294466, compound

HRID 1877405Notes

Reaction equation

HRID 1877405 reaction equation
Cl[C:2]1[C:7]([C:8]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=1[OH:31].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC#N.CC#N.CC#N.CC#N.F[P-](F)(F)(F)(F)F.[Cu+]>[N:10]1([C:8]([C:7]2[C:2]([O:31][C:22]3[CH:23]=[C:24]([C:27]([F:28])([F:29])[F:30])[CH:25]=[CH:26][C:21]=3[F:20])=[N:3][CH:4]=[CH:5][CH:6]=2)=[O:9])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 5188882-Fluoro-5-(trifluoromethyl)phenolHCID 4586912HCID 4586912, compound

Product 1

HCID 59294466HCID 59294466, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 11068737tetrakis(acetonitrile)copper(I) hexafluorophosphateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of (2-chloro-pyridin-3-yl)-(3,4-dihydro-2H-quinolin-1-yl)-methanone (50 mg, 0.18 mmol, 1.0 equiv; Example 6, Step 1) and 2-fluoro-5-trifluoromethyl-phenol (42.1 mg, 0.23 mmol, 1.3 equiv; [CAS RN 141483-15-0]) in anhydrous toluene (0.5 mL) was added caesium carbonate (176 mg, 0.54 mmol, 3.0 equiv; [CAS RN 534-17-8]) and tetrakis(acetonitrile)copper(I) hexafluorophosphate (20.1 mg, 0.054 mmol, 0.3 equiv; [CAS RN 64443-05-6]). The reaction mixture was heated by microwave irradiation to 150° C. for 1 h. Purification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column equipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps, a Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water provided 50 mg (67%) of the title compound as a light yellow solid. MS (ISP): 417.4 [M+H]+.

Workup

  1. customPurification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column
  2. customequipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps
  3. washa Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-e5f137cae02a416ba246d6a461bcf9f7
Source dataset
uspto-grants-2012_11
Patent number
US08309734B2

Reaction notes

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