Dimethylformamide → HCID 68581748, compound

HRID 915875Notes

Reaction equation

HRID 915875 reaction equation
[NH2:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([C@@H:12]3[O:27][C@H:26]([CH2:28][O:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=4[Cl:38])[C@@H:15]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=4[Cl:25])[C@@:13]3([CH3:39])[OH:14])[C:4]=2[N:5]=[CH:6][N:7]=1.C([Sn](CCCC)(CCCC)/[CH:45]=[CH:46]\[C:47]([O-:49])=[O:48])CCC.[CH3:58]N(C=O)C>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[C:3]2[C:10]([CH:45]=[CH:46][C:47]([O:49][CH3:58])=[O:48])=[CH:9][N:8]([C@@H:12]3[O:27][C@H:26]([CH2:28][O:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=4[Cl:38])[C@@H:15]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=4[Cl:25])[C@@:13]3([CH3:39])[OH:14])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 21069730HCID 21069730, compoundHCID 131726592HCID 131726592, compound

Product 1

HCID 68581748HCID 68581748, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
70 °C

Procedure

To a solution of compound 6.3 (1.25 g, 1.726 mmol) in 10 mL of anhydrous DMF was added Z-3-tributylstannylacrylate (1.1 mL, 2 eq.) (J. Am. Chem. Soc., 1993, 115, 1619), CuI (66 mg, 0.2 eq.) and PdCl2(PPh3)2 (121 mg, 0.1 eq.) at room temperature under the argon atmosphere. The reaction mixture was heated at 70° C. for 8 hr. Then the reaction mixture was cooled to room temperature and filtered through a celite pad. The filtrate was concentrated in vacuo to provide an orange-red oil as the crude product which was purified on a silica gel column with 10-30% THF in CH2Cl2 as eluent to give 995 mg 6.4 as yellow foam (yield 81%).

Workup

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. filtrationfiltered through a celite pad
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto provide an orange-red oil as the crude product which
  5. customwas purified on a silica gel column with 10-30% THF in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-942c20ea0ce14fc4a7afe5ca7a1f3683
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

Loading…