Dichloromethane → HCID 86671051, compound

HRID 1037328Notes

Reaction equation

HRID 1037328 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH:12][S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[CH2:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C(Cl)Cl.C([O-])(=O)C.[K+].I[C:46]1[C:47](=[O:74])[C:48]2[CH:49]=[CH:50][N:51]3[C:64](=[O:65])[N:63]([CH2:66][O:67][CH2:68][CH2:69][Si:70]([CH3:73])([CH3:72])[CH3:71])[N:62]=[C:52]3[C:53]=2[O:54][C:55]=1[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1.C(=O)([O-])[O-].[Na+].[Na+]>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].COCCOC>[O:65]=[C:64]1[N:51]2[CH:50]=[CH:49][C:48]3[C:47](=[O:74])[C:46]([C:2]4[CH:3]=[CH:4][C:5]([C:8]5([NH:12][S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[CH2:11][CH2:10][CH2:9]5)=[N:6][CH:7]=4)=[C:55]([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[O:54][C:53]=3[C:52]2=[N:62][N:63]1[CH2:66][O:67][CH2:68][CH2:69][Si:70]([CH3:73])([CH3:72])[CH3:71]

Participants

9

Reactant 6

HCID 6344Dichloromethane2×HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 67067901HCID 67067901, compoundHCID 86671039HCID 86671039, compound

Product 1

HCID 86671051HCID 86671051, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

To a microwave vial were added 2-methyl-propane-2-sulfinic acid [1-(5-bromo-pyridin-2-yl)-cyclobutyl]-amide (33 mg, 0.10 mmol), bis(pinacolato)diboron (30.5 mg, 0.12 mmol, [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with DCM (2.5 mg, 0.003 mmol), potassium acetate (29.4 mg, 0.30 mmol) and DME (1 mL). The reaction mixture was purged using nitrogen and heated in a microwave reactor at 100° C. for 2 h. The reaction mixture was allowed to cool to RT and 7-iodo-8-phenyl-2-(2-trimethylsilanyl-ethoxymethyl)-2H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalene-3,6-dione (53.5 mg, 0.10 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dischloropalladium(II), complex with dichloromethane (2.5 mg, 0.003 mmol), sodium carbonate solution (2 M in water, 0.2 mL, 0.4 mmol) and DME (0.5 mL) were added. The reaction mixture was purged using nitrogen and heated in a microwave reactor at 125° C. for 1 h. The reaction mixture was allowed to cool to RT, partitioned between EtOAc and water, and was filtered through a Celite® pad. The aqueous phase was extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 10% MeOH in EtOAc) to afford the title compound (54 mg, 82%). LCMS (Method B): RT=4.90 min, [M+H]+=660.

Workup

  1. customThe reaction mixture was purged
  2. temperatureto cool to RT
  3. customThe reaction mixture was purged
  4. temperatureheated in a microwave reactor at 125° C. for 1 h
  5. temperatureto cool to RT
  6. custompartitioned between EtOAc and water
  7. filtrationwas filtered through a Celite® pad
  8. extractionThe aqueous phase was extracted with EtOAc
  9. washthe combined organic extracts were washed with water and brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-afd700112bf44655a87338639dfd4042
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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