HCID 57592482, compound → HCID 57592487, compound

HRID 1784404Notes

Reaction equation

HRID 1784404 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:12](OS(C(F)(F)F)(=O)=O)=[CH:13][C:14]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16][C:15]=3[CH:22]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl-].[CH3:32][Zn+]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[C:12]([CH3:32])=[CH:13][C:14]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16][C:15]=3[CH:22]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 57592482HCID 57592482, compoundHCID 178477797HCID 178477797, compound

Product 1

HCID 57592487HCID 57592487, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of D7 (100 mg, 0.21 mmol) in dry tetrahydrofuran (2 mL) was degassed with argon for 10 minutes. To the solution Pd(PPh3)4 (30 mg) was added followed by methylzinc chloride (0.22 mL, 0.43 mmol) then heated at reflux for 30 minutes. The mixture was cooled to room temperature and quenched with water. Extraction with dichloromethane followed by purification by SCX and chromatography on silica gave the title compound D8 as a gum (56 mg). MH+ 334. 1H NMR δ (CDCl3) 2.36 (3H, s), 2.38 (3H, s), 2.47-2.66 (4H, m), 2.90-3.05 (4H, m), 6.96 (1H, s), 7.10-7.20 (2H, t), 7.83-7.92 (3H, m).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 30 minutes
  3. customquenched with water
  4. extractionExtraction with dichloromethane
  5. customfollowed by purification by SCX and chromatography on silica

Sources & evidence

ORD record
ord-120cde5cc5424870be0ea4daed0c917b
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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