2-(Trimethylstannyl)-1,3-thiazole → HCID 57194198, compound

HRID 1418372Notes

Reaction equation

HRID 1418372 reaction equation
[CH2:1]1[O:19][C:4]2([CH2:9][CH2:8][N:7]([C:10](=[O:18])[C:11]3[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1.C[Sn](C)(C)[C:22]1[S:23][CH:24]=[CH:25][N:26]=1>C1(C)C=CC=CC=1.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>[CH2:1]1[O:19][C:4]2([CH2:9][CH2:8][N:7]([C:10](=[O:18])[C:11]3[CH:16]=[CH:15][C:14]([C:22]4[S:23][CH:24]=[CH:25][N:26]=4)=[CH:13][CH:12]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 129566412-(Trimethylstannyl)-1,3-thiazoleHCID 24285503HCID 24285503, compound

Product 1

HCID 57194198HCID 57194198, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 1-(4-bromobenzoyl)-4-piperidone ethylene ketal (652 mg, 2 mmol) and trimethyl-2-thiazolylstannane (595 mg, 2.4 mmol) in degassed toluene was heated at reflux with tetrakis(triphenylphosphine)palladium(0) (200 mg, 0.17 mmol) for 16 h. The mixture was cooled, filtered through celite and evaporated. The residue was purified by flash chromatography on silica eluting with 50% ethyl acetate/hexane to yield a white solid (480 mg), MS (+CI) 331 [(M+H)+].

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through celite
  3. customevaporated
  4. customThe residue was purified by flash chromatography on silica eluting with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d4a1f604ed4947208a239b516fa996dd
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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