1,2-Dimethoxyethane → HCID 118431968, compound

HRID 2208051Notes

Reaction equation

HRID 2208051 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.COCCOC.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH:27]([C:28]2[CH:33]=[CH:32][C:31](B3OC(C)(C)C(C)(C)O3)=[CH:30][CH:29]=2)[CH2:26][C:25]([C:43]([C:49]([F:52])([F:51])[F:50])([C:45]([F:48])([F:47])[F:46])[OH:44])=[N:24]1.C(=O)([O-])[O-].[Na+].[Na+]>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.O.C(O)C>[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH:27]([C:28]2[CH:33]=[CH:32][C:31]([C:2]3[CH:7]=[N:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=3)=[CH:30][CH:29]=2)[CH2:26][C:25]([C:43]([C:49]([F:52])([F:50])[F:51])([C:45]([F:46])([F:47])[F:48])[OH:44])=[N:24]1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 114242515-Bromo-2-(methylthio)pyridineHCID 131735966HCID 131735966, compound

Product 1

HCID 118431968HCID 118431968, compoundYield 29.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
88 °C

Procedure

To 5-bromo-2-(methylthio)pyridine (14.0 mg, 0.07 mmol), were added 1,2-dimethoxyethane (1.5 mL) and Pd(PPh3)4 (8.4 mg, cat.). To the reaction mixture, were added 1-(2-chloro-phenyl)-5-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole (25.0 mg, 0.05 mmol) prepared in Step 1, ethanol 183.0 uL, and a 2N sodium carbonate solution (183.0 uL). The reaction mixture was stirred at 88° C. for 2 hours and then distilled water was added thereto. The reaction mixture was extracted with diethyl ether two times. The combined extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5) to give 8.0 mg of the titled compound as a white liquid.

Workup

  1. extractionThe reaction mixture was extracted with diethyl ether two times
  2. extractionThe combined extract
  3. washwas washed with brine
  4. dry with materialdried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow liquid residue
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-99a1b177d1b245dc80b1e902e3bebcf5
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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