Acetate → HCID 66581119, compound

HRID 1521853Notes

Reaction equation

HRID 1521853 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[CH:12]1[N:20]2[C:15]([CH2:16][S:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=32)=[C:14]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:13]=1>CN(C=O)C.C(Cl)Cl.[Pd]>[C:2]1([C:12]2[N:20]3[C:15]([CH2:16][S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=43)=[C:14]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 175AcetateHCID 11575IodobenzeneHCID 19836752HCID 19836752, compound

Product 1

HCID 66581119HCID 66581119, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

Iodo benzene (0.15 mL, 1.15 mmol, 2 eq), palladium (Il) acetate (6.4 mg, 0.03 mmol, 0.05 eq), and Cul (0.22 g, 1.15 mmol, 2 eq) are taken in pressure tube to which is added ethyl 4H-imidazo[5,1-c][1,4]benzothiazine-3-carboxylate (0.15 g, 0.576 mmol, 1 eq) taken in degassed DMF (6 mL) and the contents are heated at 140° C. for 12 h. The reaction mixture is diluted with DCM and filtered through celite. The filtrate is concentrated, passed through a plug of silica gel and concentrated to get the crude product 60 mg which is taken as such to next step. MS (ESI+): 337.2.

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate is concentrated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-863e1e3f58c9463fb54bef66eb778ea5
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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