Dimethylacetamide → HCID 68679591, compound

HRID 1172430Notes

Reaction equation

HRID 1172430 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[N:5]=[C:4]([N:17]=[C:18]2[N:22]([CH2:23][O:24][CH3:25])[CH:21]=[CH:20][S:19]2)[CH:3]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.[CH3:68][N:69](C)C(=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Zn]>[Si:10]([O:9][CH2:8][C:6]1[CH:7]=[C:2]([CH:3]=[C:4]([N:17]=[C:18]2[N:22]([CH2:23][O:24][CH3:25])[CH:21]=[CH:20][S:19]2)[N:5]=1)[C:68]#[N:69])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

8

Reactant 3

HCID 31374DimethylacetamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 68679187HCID 68679187, compound

Product 1

HCID 68679591HCID 68679591, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2.04 g of 4-bromo-6-(((tert-butyl(dimethyl)silyl)oxy)methyl)-N-(3-(methoxymethyl)-thiazol-2(3H)-ylidene)pyridin-2-amine, 379 mg of zinc cyanide, 266 mg of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 133 mg of bis(dibenzylideneacetone)palladium(0), 92 mg of zinc and 9.2 ml of N,N-dimethylacetamide was stirred at 140° C. for 3 hours. The resulting reaction mixture was diluted with ethyl acetate, and then an insoluble matter was filtered off using Celite. The filtrate was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated. The residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate=3/1) to give the title compound.

Workup

  1. customThe resulting reaction mixture
  2. filtrationan insoluble matter was filtered off
  3. washThe filtrate was washed with water and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-6e8fd87fc7554c2e80bd9dbe7f56443b
Source dataset
uspto-grants-2010_11
Patent number
US07834018B2

Reaction notes

Loading…