Cesium carbonate → HCID 66748590, compound

HRID 1622845Notes

Reaction equation

HRID 1622845 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[O:17]=[S:18]1(=[O:35])[CH2:23][CH2:22][N:21]2[CH2:24][CH2:25][CH2:26][C@@H:27]([C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=3)[C:20]2=[N:19]1.[Cl-].[Ca+2].[Cl-]>CC#N.C(O[Cu]OC(=O)C)(=O)C.N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:34][C:31]2[CH:30]=[CH:29][C:28]([C@H:27]3[C:20]4=[N:19][S:18](=[O:35])(=[O:17])[CH2:23][CH2:22][N:21]4[CH2:24][CH2:25][CH2:26]3)=[CH:33][CH:32]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 79599(4-Bromophenyl)boronic acidHCID 5284359Calcium ChlorideHCID 667484964-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol

Product 1

HCID 66748590HCID 66748590, compoundYield 6.5%

Reagents, catalysts & solvents 3

HCID 178476681HCID 178476681, compoundCatalystHCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

Diacetoxycopper (648 mg) was added to a mixture of pyridine (0.433 mL), (4-bromophenyl)boronic acid (1075 mg), cesium carbonate (581 mg) and 4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol (500 mg) in MeCN (35 mL). The mixture was stirred at room temperature under a dry atmosphere (anhydrous calcium chloride tube) for 19 hr. The insoluble, light-blue precipitates were removed by filtration through Celite-pad (eluted with EtOAc). Silica-gel was added to the filtrate and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) and concentrated in vacuo. The residue was crystallized from THF/IPE to give the title compound (50.6 mg) as colorless crystals.

Workup

  1. customThe insoluble, light-blue precipitates
  2. customwere removed by filtration through Celite-pad (eluted with EtOAc)
  3. additionSilica-gel was added to the filtrate
  4. customthe volatiles were removed in vacuo
  5. customwas purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from THF/IPE

Sources & evidence

ORD record
ord-a04619badf464fdb9d07dee2ceddc863
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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