Sodium Iodide → HCID 68872873, compound

HRID 229344Notes

Reaction equation

HRID 229344 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([NH:9][C:10]([CH3:29])([C:12](=[O:28])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][C:21]3=[O:26])=[C:16]([CH3:27])[CH:15]=2)[CH3:11])=[O:8])=[CH:4][CH:3]=1.[I-].[Na+].[CH3:32][Si:33]([C:36]#[CH:37])([CH3:35])[CH3:34].C(N(CC)CC)C>O1CCOCC1.N.O.C(#N)C.C(OCC)(=O)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1COCC1>[CH3:32][Si:33]([CH3:35])([CH3:34])[C:36]#[C:37][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]([CH3:11])([C:12](=[O:28])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][C:21]3=[O:26])=[C:16]([CH3:27])[CH:15]=2)[CH3:29])=[O:8])=[CH:4][CH:3]=1

Participants

13

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 11612692HCID 11612692, compound

Product 1

HCID 68872873HCID 68872873, compound

Reagents, catalysts & solvents 8

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 222AmmoniaSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.00 g (2.08 mmol) of 5-bromo-N-{1-methyl-1-[3-methyl-4-(3-oxomorpholin-4-yl)phenylcarbamoyl]ethyl}thiophene-2-carboxamide, 40 mg (0.208 mmol) of copper(I) iodide, 0.62 g (4.16 mmol) of sodium iodide and 0.044 ml (0.416 mmol) of N,N-dimethylethylene-1,2-diamine in 2.5 ml of dioxane is stirred at 100° C. for 20 h, cooled to room temperature, diluted with conc. ammonia and water and extracted with ethyl acetate. The combined organic phases are extracted with ethyl acetate, dried with sodium sulphate and concentrated in vac. The crude product (0.86 g) is directly reacted further. A suspension of the above crude product (0.86 g), 0.45 ml (3.26 mmol) of trimethylsilylacetylene and 0.68 ml (4.8 mmol) of triethylamine in 10 ml of acetonitrile/20 ml of THF is saturated with argon several times, and 67 mg (0.082 mmol) of PdCl2(dppf) and 15 mg (0.082 mmol) of copper(I) iodide are added. The initially reddish brown suspension becomes lemon-yellow after about 15 min. After stirring for 16 h, the mixture is diluted with ethyl acetate, washed with 5% ammonia solution, dried with sodium sulphate and concentrated in vac.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe combined organic phases are extracted with ethyl acetate
  3. dry with materialdried with sodium sulphate
  4. concentrationconcentrated in vac
  5. customThe crude product (0.86 g) is directly reacted further
  6. additionare added
  7. washwashed with 5% ammonia solution
  8. dry with materialdried with sodium sulphate
  9. concentrationconcentrated in vac

Sources & evidence

ORD record
ord-58f69a78c4514bd9a43b73026dad8b62
Source dataset
uspto-grants-2009_07
Patent number
US07563786B2

Reaction notes

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