Potassium Carbonate → N-(2-([1,1'-biphenyl]-3-yl)-2-methylpropyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide

HRID 1397444Notes

Reaction equation

HRID 1397444 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([CH3:29])([CH3:28])[CH2:9][NH:10][C:11](=[O:27])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[O:20][N:19]=3)[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.[Pd+2].ClC1C=C[C-](P(C(C)(C)C)C(C)(C)C)C=1Cl.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[C:2]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH3:29])([CH3:28])[CH2:9][NH:10][C:11](=[O:27])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[O:20][N:19]=3)[CH:13]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 69950294N-(2-(3-Bromophenyl)-2-methylpropyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide

Product 1

HCID 67379157N-(2-([1,1'-biphenyl]-3-yl)-2-methylpropyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamideYield 20.1%

Reagents, catalysts & solvents 2

HCID 178454866HCID 178454866, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of N-(2-(3-bromophenyl)-2-methylpropyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide (30 mg, 0.064 mmol) and phenyl boronic acid (39 mgs, 0.32 mmol) in THF (1.2 mL) was degassed with nitrogen. Dichloro[1,1′ bis(di-tert-butylphosphino)]ferrocene palladium (II) (5 mgs, 0.006 mmol) and 1 M potassium carbonate (1.2 mL) were added. The reaction was heated overnight at 60° C. The reaction was extracted with ethyl acetate and dried over sodium sulfate. The crude was purified by prep TLC using 30% EA/hexanes to yield N-(2-([1,1′-biphenyl]-3-yl)-2-methylpropyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide (6 mgs, yield 18%). 1H NMR (300 MHz, CDCl3) δ 8.29 (s, 1H) 8.18 (d, J=7.2 Hz, 1H), 7.81 (d, J=7.2 Hz, 1H), 7.64-7.30 (m, 10H) 5.88 (s, 1H), 3.73 (d, J=7.2 Hz, 2H), 1.48 (s, 6H). MS (ESI) m/z: Calculated for C26H22F3N3O2: 465.17. found: 466.2 (M+H)+.

Workup

  1. extractionThe reaction was extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe crude was purified by prep TLC

Sources & evidence

ORD record
ord-cef26ce643e74d9b867aee6deb72f09c
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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