Potassium Carbonate → Benzyl (2'-((4-isopropyl-3-methylphenyl)carbamoyl)-6-methoxy-[3,4'-bipyridin]-5-yl)carbamate

HRID 2283475Notes

Reaction equation

HRID 2283475 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][N:4]=1.Br[C:30]1[CH:35]=[CH:34][N:33]=[C:32]([C:36]([NH:38][C:39]2[CH:44]=[CH:43][C:42]([CH:45]([CH3:47])[CH3:46])=[C:41]([CH3:48])[CH:40]=2)=[O:37])[CH:31]=1.C([O-])([O-])=O.[K+].[K+]>CCO.C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:45]([C:42]1[CH:43]=[CH:44][C:39]([NH:38][C:36]([C:32]2[CH:31]=[C:30]([C:6]3[CH:5]=[N:4][C:3]([O:2][CH3:1])=[C:8]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:7]=3)[CH:35]=[CH:34][N:33]=2)=[O:37])=[CH:40][C:41]=1[CH3:48])([CH3:47])[CH3:46]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 16062737Benzyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ylcarbamateHCID 1182507534-bromo-N-(4-isopropyl-3-methylphenyl)picolinamide

Product 1

HCID 118261435Benzyl (2'-((4-isopropyl-3-methylphenyl)carbamoyl)-6-methoxy-[3,4'-bipyridin]-5-yl)carbamateYield 90%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of benzyl (2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)carbamate (180 mg, 0.47 mmol) in EtOH (4 mL) and toluene (16 mL) was added 4-bromo-N-(4-isopropyl-3-methylphenyl)picolinamide (0.23 g, 0.70 mmol), Pd(PPh3)4 (5.4 mg, 0.046 mmol), and 2M K2CO3 in water (0.46 mL). The mixture was stirred at 100° C. overnight under nitrogen. After cooling to room temperature and evaporation of the solvent, the residue was purified by combi-flash (ISCO, 40 g silica, UV254, 3:1 pet ether/ethyl acetate) to afford benzyl (2′-((4-isopropyl-3-methylphenyl)carbamoyl)-6-methoxy-[3,4′-bipyridin]-5-yl)carbamate (216 mg, 90% yield) as a yellow solid: MS (ES) m/z 511 (M+H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customevaporation of the solvent
  3. customthe residue was purified by combi-flash (ISCO, 40 g silica, UV254, 3:1 pet ether/ethyl acetate)

Sources & evidence

ORD record
ord-9ddd8e18c0a44b09b40997323a9bfa99
Source dataset
uspto-grants-2015_09
Patent number
US09145393B2

Reaction notes

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