Dichloromethane → HCID 86671050, compound

HRID 1037326Notes

Reaction equation

HRID 1037326 reaction equation
I[C:2]1[C:3](=[O:30])[C:4]2[CH:5]=[CH:6][N:7]3[C:20](=[O:21])[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[N:18]=[C:8]3[C:9]=2[O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC1(C)C(C)(C)OB([C:39]2[CH:44]=[CH:43][C:42]([C:45]3([NH:49][S:50]([C:52]([CH3:55])([CH3:54])[CH3:53])=[O:51])[CH2:48][O:47][CH2:46]3)=[CH:41][CH:40]=2)O1.ClCCl.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:21]=[C:20]1[N:7]2[CH:6]=[CH:5][C:4]3[C:3](=[O:30])[C:2]([C:39]4[CH:40]=[CH:41][C:42]([C:45]5([NH:49][S:50]([C:52]([CH3:55])([CH3:54])[CH3:53])=[O:51])[CH2:48][O:47][CH2:46]5)=[CH:43][CH:44]=4)=[C:11]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[O:10][C:9]=3[C:8]2=[N:18][N:19]1[CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 670678002-Methyl-propane-2-sulfinic acid {3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenyl]-oxetan-3-yl}-amideHCID 86671039HCID 86671039, compound

Product 1

HCID 86671050HCID 86671050, compoundYield 70%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
125 °C

Procedure

A mixture of 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), 2-methyl-propane-2-sulfinic acid {3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenyl]-oxetan-3-yl}-amide (57 mg, 0.15 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with dichloromethane (4 mg, 0.005 mmol), sodium carbonate solution (2 M in water, 0.3 mL, 0.6 mmol) and DME (2 mL) 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 and was partitioned between EtOAc and water. 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 5 (% MeOH in EtOAc) to afford the title compound (46 mg, 70%) as a yellow gum. LCMS (Method H): RT=3.95 min, [M+H]+=661.

Workup

  1. customwas purged
  2. temperatureto cool to RT
  3. customwas partitioned between EtOAc and water
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined organic extracts were washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-30e183dde44a4fdba746da42c531f780
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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