1,2-Dimethoxyethane → HCID 118432020, compound

HRID 2208083Notes

Reaction equation

HRID 2208083 reaction equation
Br[C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1.COCCOC.[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=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>[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[N:23]1[CH:27]([C:28]2[CH:29]=[CH:30][C:31]([C:2]3[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=3)=[CH:32][CH:33]=2)[CH2:26][C:25]([C:43]([C:49]([F:52])([F:51])[F:50])([C:45]([F:46])([F:47])[F:48])[OH:44])=[N:24]1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 12010033-Bromo-2-methylpyridineHCID 131735967HCID 131735967, compound

Product 1

HCID 118432020HCID 118432020, compoundYield 9.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
88 °C

Procedure

To 3-bromo-2-methylpyridine (25.0 mg, 0.14 mmol), were added 1,2-dimethoxyethane (1.5 mL) and Pd(PPh3)4 (8.5 mg, cat.). To the reaction mixture, were added 1-(2,4-difluoro-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 (40.0 mg, 0.07 mmol) prepared in Step 1, ethanol 364.0 uL, and a 2N sodium carbonate solution (364.0 uL). The reaction mixture was stirred at 88° C. for 2 hours. Distilled water was added to the reaction mixture, which was then 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 3.3 mg of the titled compound as a yellow liquid.

Workup

  1. extractionwas then 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-67c1ca1b9058489b9a85545a437f94b3
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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