Cesium carbonate → HCID 59302498, compound

HRID 2237621Notes

Reaction equation

HRID 2237621 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]2[CH2:21][CH2:20][CH:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:18][CH2:17]2)[CH:5]=[CH:6][C:7]=1OS(C(F)(F)F)(=O)=O.[Si:27]([O:34][CH2:35][CH2:36][NH2:37])([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCCCC.CCOC(C)=O>[C:30]([Si:27]([CH3:29])([CH3:28])[O:34][CH2:35][CH2:36][NH:37][C:7]1[CH:6]=[CH:5][C:4]([CH:16]2[CH2:21][CH2:20][CH:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:18][CH2:17]2)=[CH:3][C:2]=1[F:1])([CH3:33])([CH3:32])[CH3:31]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 529218(2-Aminoethoxy)(tert-butyl)dimethylsilaneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 59302517HCID 59302517, compound

Product 1

HCID 59302498HCID 59302498, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×HCID 8900HeptaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 2-(4-(3-fluoro-4-(trifluoromethylsulfonyloxy)phenyl)cyclohexyl)acetate (190 mg, 0.477 mmol), 2-{[tert-butyl(dimethyl)silyl]oxy}ethanamine (100 mg, 0.572 mmol), cesium carbonate (171 mg, 0.525 mmol), palladium acetate (11 mg, 0.048 mmol) and (X-PHOS) (23 mg, 0.048 mmol) in toluene (5 mL), under nitrogen, was heated in a sealed tube at 120° C. for 16 hours. The reaction was cooled, diluted into EtOAc, washed with water (2×), saturated aqueous brine, dried over sodium sulfate and concentrated to afford a dark oil. Chromatography (12 g silica gel column, 3-15% EtOAc:heptane) afforded methyl 2-(4-(4-(2-(tert-butyldimethyl-silyloxy)ethylamino)-3-fluorophenyl)-cyclohexyl)acetate as a light-yellow oil, 110 mg. 1H NMR (400 MHz, CDCl3); δ 7.2 (m, 1H), 6.95 (m, 1H), 6.8 (m, 1H), 3.8 (m, 2H), 3.64 (s, 3H), 3.2 (m, 2H), 2.5, 2.3 (m, 1H), 2.4, 2.2 (d, 2H), 1.85 (m, 2H), 1.64 (m, 5H), 1.4 (m, 1H), 1.1 (m, 1H), 0.88 (s, 9H), 0.06 (s, 6H). m/z=424.2 (M+1).

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with water (2×), saturated aqueous brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto afford a dark oil

Sources & evidence

ORD record
ord-925d65be0d0849959c7155742794791c
Source dataset
uspto-grants-2010_05
Patent number
US07718645B2

Reaction notes

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