Potassium Phosphate, Tribasic → HCID 58487135, compound

HRID 2272231Notes

Reaction equation

HRID 2272231 reaction equation
Br[C:2]1[C:12]([CH3:13])=[CH:11][C:5]2[O:6][CH2:7][C:8]([CH3:10])([CH3:9])[C:4]=2[CH:3]=1.FC1(F)OC2C=C(C)C(C3N=C[C:27]([NH:30][C:31](=O)[C:32]4[CH:37]=[CH:36]C=CC=4F)=[N:28]C=3)=CC=2O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C.O1CCOCC1.O>[CH3:9][C:8]1([CH3:10])[CH2:7][O:6][C:5]2[CH:11]=[C:12]([CH3:13])[C:2]([C:32]3[CH:37]=[CH:36][C:27]([NH2:28])=[N:30][CH:31]=3)=[CH:3][C:4]1=2

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 18699201HCID 18699201, compoundHCID 58486754N-(5-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)pyrazin-2-yl)-2-fluorobenzamide

Product 1

HCID 58487135HCID 58487135, compoundYield 90.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5-bromo-3,3,6-trimethyl-2,3-dihydrobenzo[b]furan (171) (241 mg, 1 mmol), 2-aminopyridine-5-boronic acid pinacol ester (11) (330 mg, 1.5 mmol), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (106 mg), and K3PO4 (636 mg) in 3 ml ACN, 3 ml dioxane, 1.5 ml H2O was bubbled with argon before heated at 85° C. for 2.5 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine. Org. phase was dried over Na2SO4, concentrated and then subjected silica gel column purification to give 231 mg 5-(3,3,6-trimethyl-2,3-dihydrobenzo[3,4-b]furan-5-yl)-2-pyridylamine (172) (yield: 90.8%, purity>95%) as thick yellow oil.

Workup

  1. customwas bubbled with argon
  2. temperatureAfter cooling down to r.t.
  3. washwashed with aq. NaHCO3 and brine
  4. dry with materialphase was dried over Na2SO4
  5. concentrationconcentrated
  6. customsubjected silica gel column purification

Sources & evidence

ORD record
ord-d6c377934fc54b86866510ec79ebc4a1
Source dataset
uspto-grants-2015_09
Patent number
US09120751B2

Reaction notes

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