HCID 59364203, compound → HCID 59364223, compound

HRID 1810118Notes

Reaction equation

HRID 1810118 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:8]=[C:7]2I)([O-:3])=[O:2]>CN(C=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:19]1([CH3:22])[CH:18]=[CH:17][C:16]([S:13]([N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[CH:12][CH:11]=3)[C:7]([C:7]3[C:6]4[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)[N:9]([S:13]([C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=4)(=[O:15])=[O:14])[CH:8]=3)=[CH:8]2)(=[O:15])=[O:14])=[CH:21][CH:20]=1

Participants

5

Reactant 1

HCID 59364203HCID 59364203, compound

Product 1

HCID 59364223HCID 59364223, compoundYield 100.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 222 (0.331 g, 0.748 mmol), crude 206 (0.42 g, 0.748 mmol), catalytic amount of CuI and tetrakis(triphenylphosphine)palladium in DMF (10 mL) was degassed with argon for 10 min (Scheme 16). The mixture was brought to 50° C. and stirred for 5 h. The solvent was removed in vacuo and the residue was purified by flash chromatography (20% ethyl acetate/hexane V:V) to yield 223 (0.22 g, 50%). 1H NMR (CDCl3): 2.36 (s, 3H), 2.38 (s, 3H), 7.26-7.33 (m, 5H), 7.43 (t, 1H. J=7.8), 7.56 (d, 1H, J=7.8), 7.80 (s, 1H), 7.84-7.87 (m, 4H), 7.92 (s, 1H), 8.11 (d, 1H, J=8.4), 8.17 (d, 1H, J=9.1), 8.28 (d, 1 H, J=9.0), 8.48 (s, 1H).

Workup

  1. customwas brought to 50° C.
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by flash chromatography (20% ethyl acetate/hexane V:V)

Sources & evidence

ORD record
ord-14895358ce7249d3a9bbbed5169bf178
Source dataset
uspto-grants-2013_01
Patent number
US08362066B2

Reaction notes

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