1,4-Dioxane → HCID 59443489, compound

HRID 1035637Notes

Reaction equation

HRID 1035637 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=4)=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]=2[O:26][CH3:27])[CH:5]=[CH:6][CH:7]=1.C1CCN2C(=NCCC2)CC1.[CH3:39][S:40]([NH2:43])(=[O:42])=[O:41].[O:44]1CCOC[CH2:45]1>ClCCl.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:27][O:26][C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)[CH:13]=2)[C:8]=1[C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:45]([NH:43][S:40]([CH3:39])(=[O:42])=[O:41])=[O:44]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68482688HCID 68482688, compound

Product 1

HCID 59443489HCID 59443489, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(3-Iodophenyl)-2-methoxy-6-(3-methoxyphenyl)naphthalene (150 mg, 0.32 mmol, 1 eq), Mo(C0)6 (85 mg, 0.32 mmol, 1 eq), Pd(OAc)2 (7.2 mg, 0.03 mmol, 0.01 eq), DBU (145 μl, 0.96 mmol, 3 eq), methylsulfonamide (91.7 mg, 0.96 mmol, 3 eq) and 1,4-dioxane (1 ml) are charged into a reaction vessel. The reaction is performed in a microwave oven at 110° C. for 15 min. After cooling, the reaction mixture is dissolved in dichloromethane, and purification by column chromatography with dichloromethane and 2% methanol as eluents was performed. The compound was obtained in quantitative yield.

Workup

  1. temperatureAfter cooling
  2. custompurification by column chromatography with dichloromethane and 2% methanol as eluents
  3. customThe compound was obtained in quantitative yield

Sources & evidence

ORD record
ord-08c5f657f9a7459da66085b2e0e9208e
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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