Potassium Carbonate → HCID 70005328, compound

HRID 1860529Notes

Reaction equation

HRID 1860529 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([CH:7]=[CH:8][Sn](CCCC)(CCCC)CCCC)[C@@H:3]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29].C(=O)([O-])[O-].[K+].[K+].Br[C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=1)[C:41]#[N:42]>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCCC1>[C:41]([C:40]1[CH:39]=[C:38]([CH:8]=[CH:7][C@@H:4]2[CH2:5][CH2:6][C:2](=[O:1])[C@H:3]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH:45]=[CH:44][CH:43]=1)#[N:42]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 233813-BromobenzonitrileHCID 70006814HCID 70006814, compound

Product 1

HCID 70005328HCID 70005328, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Wang resin bound trans-7-[2-oxo-5-(2-tributylstannanyl-vinyl)-cyclopentyl]-heptanoic acid (the compound of Preparation 1, Step F, 70 mg, 0.05 mmol, 1 eq), tris(dibenzylideneacetone)dipalladium(0) (18.2 mg, 0.02 mmol, 0.4 eq), diisopylethylamine (12.8 mg, 0.099 mmol, 2 eq), potassium carbonate (10 mg) and 3-bromo-benzonitrile (36.2 mg, 0.199 mmol, 4 eq) were placed in a well of a deep-well plate, and tetrahydrofuran was added until resin was just wet. The slurry was shaken at room temperature overnight. The resin was filtered and washed with N,N-dimethylformamide and methanol. It was repeatedly swollen with dichloromethane and shrunk with methanol. The resin was finally washed with diethyl ether to remove methanol. Cleavage of the product with trifluoroacetic acid as described in Step B of Example 3 with 90% trifluoroacetic acid in water gave the title compound of Example 66.

Workup

  1. additionwas added until resin
  2. filtrationThe resin was filtered
  3. washwashed with N,N-dimethylformamide and methanol
  4. washThe resin was finally washed with diethyl ether
  5. customto remove methanol

Sources & evidence

ORD record
ord-c8bf9a74c8f448aba799a42d5d0c4a7a
Source dataset
uspto-grants-2003_03
Patent number
US06531485B2

Reaction notes

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