2-(Trimethylsilyl)-5-(trimethylstannyl)thiazole → HCID 67237468, compound

HRID 1028105Notes

Reaction equation

HRID 1028105 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:19][C:20](=[O:22])[CH3:21])[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.C[Si](C)(C)[C:25]1[S:26][C:27]([Sn](C)(C)C)=[CH:28][N:29]=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.O1CCOCC1>[S:26]1[C:27]([C:2]2[CH:3]=[C:4]([NH:19][C:20](=[O:22])[CH3:21])[CH:5]=[C:6]([NH:8][C:9]3[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=3)[CH:7]=2)=[CH:28][N:29]=[CH:25]1

Participants

5

Reactant 2

HCID 136620692-(Trimethylsilyl)-5-(trimethylstannyl)thiazoleHCID 71075523HCID 71075523, compound

Product 1

HCID 67237468HCID 67237468, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

N-(3-bromo-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)acetamide (150 mg, 0.400 mmol), 2-(trimethylsilyl)-5-(trimethylstannanyl)-1,3-thiazole (141 mg, 0.440 mmol) (prepared using literature procedure: Dondoni, A.; Mastellari, A. R.; Medici, A.; Negrini, E.; Pedrini, P. Synthesis 1986, 9, 757-760) and Pd(Ph3P)4 (46.2 mg, 0.040 mmol) were placed in a nitrogen purged microwave vial. Dioxane (2 mL) was added and the resultant solution was purged for 10 minutes with nitrogen gas. The reaction mixture was heated to 90° C. for 15 h. Note: Under the reaction conditions the TMS group is removed. The reaction mixture was concentrated and directly purified by column chromatography to yield 130 mg of N-[3-(1,3-thiazol-5-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl]acetamide (0.343 mmol, 86%) as a yellow powder.

Workup

  1. customthe resultant solution was purged for 10 minutes with nitrogen gas
  2. customUnder the reaction conditions the TMS group
  3. customis removed
  4. concentrationThe reaction mixture was concentrated
  5. customdirectly purified by column chromatography

Sources & evidence

ORD record
ord-4112053bd56647ba9c43582d8acdf77c
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

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