Acetonitrile → 5-(6,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)pyridin-2-amine

HRID 627876Notes

Reaction equation

HRID 627876 reaction equation
Br[C:2]1[S:15][C:5]2[C:6]3[N:14]=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]=2[CH:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][N:18]=1.C(#N)C>C(=O)([O-])[O-].[Na+].[Na+].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>[N:14]1[C:6]2[C:5]3[S:15][C:2]([C:20]4[CH:21]=[CH:22][C:17]([NH2:16])=[N:18][CH:19]=4)=[CH:3][C:4]=3[CH2:10][CH2:9][O:8][C:7]=2[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 6342AcetonitrileHCID 22396308(6-Aminopyridin-3-yl)boronic acidHCID 579004919-Bromo-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepine

Product 1

HCID 442423665-(6,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)pyridin-2-amineYield 36%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 9-bromo-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepine (113 mg, 0.400 mmol), 2-aminopyridine-5-boronic acid, pinacol ester (96.8 mg, 0.440 mmol) and bis(triphenylphosphine)palladium(II) chloride (14.0 mg, 0.0200 mmol) in 1.0 M of sodium carbonate in water (0.500 mL) and acetonitrile (3 mL, 60 mmol) was degassed and microwaved on 300 watts at 140° C. for 20 minutes. The reaction mixture was partitioned between ethyl acetate and water and filtered from inorganic salts. The organic layer was washed with water, brine, dried over MgSO4 and evaporated to dryness. The crude residue was purified on silicagel column, eluting with 50% of ethyl acetate in methylene chloride to give 142 (yield 43 mg, 36%).

Workup

  1. custommicrowaved on 300 watts at 140° C. for 20 minutes
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. filtrationfiltered from inorganic salts
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customThe crude residue was purified on silicagel column
  8. washeluting with 50% of ethyl acetate in methylene chloride

Sources & evidence

ORD record
ord-c485172b705c495387b5488acd674ab5
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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