Potassium Carbonate → tert-Butyl 4-(1-(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethylidene)piperidine-1-carboxylate

HRID 1666478Notes

Reaction equation

Br[C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=2)[CH:17]=1)=[C:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[CH3:33]B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Ag]=O>[F:30][C:29]([F:32])([F:31])[C:26]1[CH:27]=[CH:28][C:23]([O:22][C:18]2[CH:17]=[C:16]([C:2](=[C:3]3[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]3)[CH3:33])[CH:21]=[CH:20][CH:19]=2)=[N:24][CH:25]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of tert-butyl 4-(bromo(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate (Example 71, step 2) (420 mg, 0.818 mmol) in toluene (10 mL), under N2 was added methyl boronic acid (54 mg, 0.900 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (60 mg, 0.0818 mmol), potassium carbonate (226 mg, 1.64 mmol) and silver oxide (379 mg, 1.64 mmol). The reaction was heated to 85° C. overnight. The reaction was cooled down and filtered. The filtrate was washed with water and dried over MgSO4. Purification by silica gel column chromatography (0-5% MeOH/CH2Cl2) gave the title compound (291 mg, 79% yield).

Workup

temperatureThe reaction was cooled down
filtrationfiltered
washThe filtrate was washed with water
dry with materialdried over MgSO4
customPurification by silica gel column chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-c14456802d7d425c9994544548be7e19
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044052B2

Reaction notes

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