1,2-Dimethoxyethane → HCID 53250501, compound

HRID 509620Notes

Reaction equation

HRID 509620 reaction equation
Br[C:2]1[N:3]=[C:4]([CH2:8][CH2:9][C:10]2[N:21]=[C:13]3[C:14]([O:19][CH3:20])=[CH:15][CH:16]=[C:17]([CH3:18])[N:12]3[N:11]=2)[N:5]([CH3:7])[CH:6]=1.[O:22]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23]1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>O.[Cl-].[Na+].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.CCOC(C)=O>[O:22]1[CH:26]=[CH:25][C:24]([C:2]2[N:3]=[C:4]([CH2:8][CH2:9][C:10]3[N:21]=[C:13]4[C:14]([O:19][CH3:20])=[CH:15][CH:16]=[C:17]([CH3:18])[N:12]4[N:11]=3)[N:5]([CH3:7])[CH:6]=2)=[CH:23]1

Participants

9

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 67258554HCID 67258554, compound

Product 1

HCID 53250501HCID 53250501, compoundYield 14.8%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

A glass vial was charged with 2-[2-(4-Bromo-1-methyl-1H-imidazol-2-yl)-ethyl]-8-methoxy-5-methyl-[1,2,4]triazolo[1,5-a]pyridine (70 mg, 0.20 mmol), furan-3-boronic acid (33.6 mg, 0.30 mmol), 1,2-dimethoxyethane (0.8 mL), 1M solution of sodium carbonate in water (0.3 mL) and the slurry was deoxygenated by bubbling argon through then tetrakis(triphenylphosphine)palladium(0) (5.2 mg, 0.0045 mmol) was added and the vessel sealed and heated at 110° C. for 12 hours. EtOAc (3 mL) was added followed by brine solution (2 mL). The organic layer was separated and the volatiles removed in vacuo. The residue was purified by column chromatography on silica gel (gradient 100% EtOAc to EtOAc:MeOH, 7:3) to yield the title compound (10 mg, 10%). LCMS (MH+): m/z=338.1, tR (minutes, method B)=0.41

Workup

  1. customthe slurry was deoxygenated
  2. additionwas added
  3. customthe vessel sealed
  4. customThe organic layer was separated
  5. customthe volatiles removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel (gradient 100% EtOAc to EtOAc:MeOH, 7:3)

Sources & evidence

ORD record
ord-0412bf5fab1f4b0d9964a1fb4649be0c
Source dataset
uspto-grants-2015_08
Patent number
US09096589B2

Reaction notes

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