Cesium fluoride → HCID 21107411, compound

HRID 1765537Notes

Reaction equation

HRID 1765537 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:22])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8].[CH2:23](C([Sn])=C(CCCC)CCCC)[CH2:24]CC.[F-].[Cs+]>C1(C)C=CC=CC=1.CC(C)=O.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>[Cl:22][C:5]1[CH:4]=[CH:3][C:2]([CH:23]=[CH2:24])=[CH:21][C:6]=1[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8]

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 79213085-bromo-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamideHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 21107411HCID 21107411, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

A solution of 5-bromo-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide (prepared as described in WO 00/61569) (1.0 g), tetrakis(triphenylphosphine)palladium(0) (96 mg) and tributylvinyltin (1.15 mL) in toluene (15 mL) was heated at reflux for 3 hours, then cooled to room temperature, diluted with acetone (30 mL) and treated with cesium fluoride (10% aq, 10 mL) at room temperature for 2 hours. The resulting mixture was filtered through celite with further washing with toluene and concentrated. Water was added and the mixture was extracted with ethyl acetate. The combined organic phases were washed with water, dried over anhydrous magnesium sulfate and concentrated. The resulting oil was purified by column chromatography (ethyl acetate:isohexane 100:1 to 80:20) to give the sub-titled compound as a white solid (0.87 g).

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationThe resulting mixture was filtered through celite
  3. washwith further washing with toluene
  4. concentrationconcentrated
  5. additionWater was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe combined organic phases were washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe resulting oil was purified by column chromatography (ethyl acetate:isohexane 100:1 to 80:20)

Sources & evidence

ORD record
ord-0f183ac150ef4e87ae2e89f6f80517a9
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

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