Pyridine → HCID 66747924, compound

HRID 1405812Notes

Reaction equation

HRID 1405812 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[O:11]=[S:12]1(=[O:29])[CH2:17][CH2:16][N:15]2[CH2:18][CH2:19][CH2:20][CH:21]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[C:14]2=[N:13]1.N1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O.C(O[Cu]OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:28][C:25]2[CH:24]=[CH:23][C:22]([CH:21]3[C:14]4=[N:13][S:12](=[O:29])(=[O:11])[CH2:17][CH2:16][N:15]4[CH2:18][CH2:19][CH2:20]3)=[CH:27][CH:26]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 10796Cesium carbonateHCID 742994-Chlorophenylboronic acidHCID 667477204-(2,2-Dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol

Product 1

HCID 66747924HCID 66747924, compoundYield 16.5%

Reagents, catalysts & solvents 3

HCID 178476681HCID 178476681, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 4-chlorophenylboronic acid (167 mg), 4-(2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (100 mg), pyridine (0.087 mL), diacetoxycopper (130 mg), and cesium carbonate (116 mg) in DMSO (3.0 mL) was stirred at room temperature for 24 hr. The mixture was diluted with water, and extracted with EtOAc (40 mL). The organic layer was washed with 0.1N NaOH aq. (2×40 mL) and then brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with MeOH in EtOAc) to give the title compound (23.0 mg) as a white solid.

Workup

  1. extractionextracted with EtOAc (40 mL)
  2. washThe organic layer was washed with 0.1N NaOH aq. (2×40 mL)
  3. dry with materialbrine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, eluted with MeOH in EtOAc)

Sources & evidence

ORD record
ord-f72c2083e0c54a7fa59ed58a74903ca0
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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