Water → HCID 89649331, compound

HRID 2207611Notes

Reaction equation

HRID 2207611 reaction equation
Br[C:2]1[C:7]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:6][N:5]=[C:4]([C:13]2[CH2:17][CH2:16][C:15]3([CH2:21][CH2:20][N:19]([CH3:22])[C:18]3=[O:23])[N:14]=2)[CH:3]=1.O.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(Cl)Cl.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>[C:9]([O:8][C:7]1[C:2]([C:30]2[CH:31]=[CH:32][C:27]([C:26]([F:37])([F:36])[F:25])=[CH:28][CH:29]=2)=[CH:3][C:4]([C:13]2[CH2:17][CH2:16][C:15]3([CH2:21][CH2:20][N:19]([CH3:22])[C:18]3=[O:23])[N:14]=2)=[N:5][CH:6]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

10

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 89649192HCID 89649192, compound

Product 1

HCID 89649331HCID 89649331, compoundYield 37.1%

Reagents, catalysts & solvents 5

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-(4-bromo-5-tert-butoxy-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one (which may be prepared as described in Description 36) (605 mg, 1.59 mmol) in 1,2-dimethoxyethane (16 mL) was added water (4 mL), [4-(trifluoromethyl)phenyl]boronic acid (332.38 mg, 1.75 mmol) and sodium carbonate (505.87 mg, 4.77 mmol). The mixture was degassed with a stream of nitrogen and bis(triphenylphosphine)-palladium (II) dichloride (55.83 mg, 0.0800 mmol) was added. The mixture was heated to 120° C. over 15 minutes in a microwave. The reaction mixture was diluted with DCM and a little water and the phases separated with a hydrophobic frit. The organic filtrate was evaporated to yield a brown gum, (798 mg). Column chromatography (0-10% MeOH in EtOAc) yielded 2-[5-tert-butoxy-4-[4-(trifluoro-methyl)-phenyl]-2-pyridyl]-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one (263 mg, 0.5904 mmol, 37.1% yield) as a yellow foam;

Workup

  1. additionwas added
  2. customa little water and the phases separated with a hydrophobic frit
  3. customThe organic filtrate was evaporated
  4. customto yield a brown gum, (798 mg)

Sources & evidence

ORD record
ord-e0ebbd7913d94fdda39640dd6e6bc019
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

Loading…