Acetonitrile → HCID 58204336, compound

HRID 2044232Notes

Reaction equation

HRID 2044232 reaction equation
I[C:2]1[N:3]=[C:4]2[C:10]3[CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:14][C:9]=3[O:8][CH2:7][CH2:6][N:5]2[CH:19]=1.[CH:20]([N:23]1[C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:25]=[N:24]1)([CH3:22])[CH3:21].ClCCl.C([O-])(=O)C.[K+].C(#N)C>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:20]([N:23]1[C:27]([C:2]2[N:3]=[C:4]3[C:10]4[CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:14][C:9]=4[O:8][CH2:7][CH2:6][N:5]3[CH:19]=2)=[CH:26][CH:25]=[N:24]1)([CH3:22])[CH3:21]

Participants

8

Reactant 5

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 567767101-(Propan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 58204419Methyl 2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-10-carboxylate

Product 1

HCID 58204336HCID 58204336, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Procedure

A mixture of methyl 2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-10-carboxylate (370.1 mg, 1.000 mmol), 1-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (354 mg, 1.50 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (40.8 mg, 0.0500 mmol) and 2.0 M of Potassium acetate in water (1.00 mL) in Acetonitrile (12 mL, 230 mmol) was degassed. The reaction was microwaved on 200 watts, 140° C. for 30 minutes. The reaction mixture was partitioned between water and ethyl acetate, filtered, the organic layer was washed with water, brine, dried over MgSO4 and concentrated in vacuum. The residue was purified on 12 g silica column eluting with 35-40% ethyl acetate in heptane. Yield 119 mg (34%). MS: (ESI+): 353.1.

Workup

  1. customwas degassed
  2. customThe reaction was microwaved on 200 watts, 140° C. for 30 minutes
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. filtrationfiltered
  5. washthe organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuum
  8. customThe residue was purified on 12 g silica column
  9. washeluting with 35-40% ethyl acetate in heptane

Sources & evidence

ORD record
ord-dac5082417404191b672d8e15484a6b4
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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