1,4-Dioxane → HCID 86705038, compound

HRID 1477837Notes

Reaction equation

HRID 1477837 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([N:13]2[C:21]3[C:16](=[C:17]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)[C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1.O1CCO[CH2:40][CH2:39]1>C(=O)(O)[O-].[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]>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([N:13]3[C:21]4[C:16](=[C:17]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=[CH:19][CH:20]=4)[CH:15]=[CH:14]3)([CH2:39][CH3:40])[C:9]([O:11][CH3:12])=[O:10])[CH:3]=2)[CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 2734370(3-Methoxyphenyl)boronic acidHCID 68175417HCID 68175417, compound

Product 1

HCID 86705038HCID 86705038, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 516892Sodium BicarbonateSolvent

Procedure

[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (17 mg, 0.24 mmol) was added to a stirred solution of 10a (50 mg, 0.114 mmol) and 3-methoxyphenylboronic acid (21 mg, 0.140 mmol) in dioxane (0.6 mL) and saturated aqueous sodium bicarbonate (0.125 mL) at rt. The resulting solution was irradiated in a microwave reactor at 120° C. for 10 min. After cooling to rt, the reaction mixture was filtered through a short column of CELITE® eluting with EtOAc. The resulting crude oil was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier), followed by lyophilization of the purified fractions to afford the title compound 78. m/z (ES) 465 (MH)+; IP=C rating.

Workup

  1. customThe resulting solution was irradiated in a microwave reactor at 120° C. for 10 min
  2. filtrationthe reaction mixture was filtered through a short column of CELITE®
  3. washeluting with EtOAc
  4. customThe resulting crude oil was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier)

Sources & evidence

ORD record
ord-c3fde617594e4c0b8c61f3c9fdd37d95
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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