Water → HCID 86649111, compound

HRID 2364831Notes

Reaction equation

HRID 2364831 reaction equation
C([N:4]1[C@@H:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)[CH2:7][CH2:6][C@@H:5]1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([N+:26]([O-:28])=[O:27])[CH:20]=1)C=C.O>C(#N)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C@H:8]2[CH2:7][CH2:6][C@H:5]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([N+:26]([O-:28])=[O:27])[CH:20]=3)[NH:4]2)=[CH:10][C:11]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 2

HCID 962WaterHCID 86649110HCID 86649110, compound

Product 1

HCID 86649111HCID 86649111, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

The product from Example 115A (2.0 g, 4.74 mmol) was dissolved in acetonitrile (40 mL) and water (4 mL) and treated with Tris(triphenylphosphine)rhodium(I) chloride (0.219 g, 0.237 mmol). The mixture was heated at 100° C. and nitrogen was bubbled through the solution for 3 hours. The mixture was partitioned between 5% sodium bicarbonate solution and ethyl acetate, then the organics were concentrated and the product purified by combiflash 80 g silica column eluting with dichloromethane to give 1.33 g (74%) of the title compound.

Workup

  1. customnitrogen was bubbled through the solution for 3 hours
  2. customThe mixture was partitioned between 5% sodium bicarbonate solution and ethyl acetate
  3. concentrationthe organics were concentrated
  4. customthe product purified by combiflash 80 g silica column
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-d0e83fe85c534f7ca50e0f3e9f927bc6
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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