Potassium Carbonate → 2-{1-[Tri(propan-2-yl)silyl]-1H-pyrrol-3-yl}-1,3-thiazole

HRID 2222273Notes

Reaction equation

HRID 2222273 reaction equation
[CH:1]([Si:4]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[N:5]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6]1)([CH3:3])[CH3:2].Br[C:20]1[S:21][CH:22]=[CH:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1.CO.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>[CH:1]([Si:4]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[N:5]1[CH:9]=[CH:8][C:7]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[CH:6]1)([CH3:3])[CH3:2]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 27633031-(Triisopropylsilyl)pyrrole-3-boronic acid

Product 1

HCID 693030142-{1-[Tri(propan-2-yl)silyl]-1H-pyrrol-3-yl}-1,3-thiazole

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of crude 1-(triisopropylsilyl)-1H-pyrrol-3-ylboronic acid, 2-bromo-1,3-thiazole (0.206 g, 1.26 mmol) and potassium carbonate (0.174 g, 1.26 mmol) in benzene (10 mL), methanol (1 mL) and water (1 mL) was degassed with argon for 15 min. Tetrakis(triphenylphosphine)palladium(0) (40 mg, 0.034 mmol) was added and the reaction mixture was degassed a further 15 min before stirring at 70° C. for 14 h. The reaction mixture was quenched with water (30 mL) then extracted with EtOAc (3×30 mL) and washed with brine. The combined organic phase was dried over Na2SO4 and concentrated in vacuo. The crude residue was chromatographed on silica gel eluting with EtOAc:hexane (1:1) to afford 2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]-1,3-thiazole as a brown oil. 1H NMR (CD3Cl, 300 MHz) δ 7.68 (d, 1H), 7.37-7.36 (m, 1H), 7.08 (d, 1H), 7.76-7.75 (m, 1H), 6.70 (dd, 1H), 1.46 (h, 3H) 1.09 (d, 18H).

Workup

  1. customthe reaction mixture was degassed a further 15 min
  2. customThe reaction mixture was quenched with water (30 mL)
  3. extractionthen extracted with EtOAc (3×30 mL)
  4. washwashed with brine
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was chromatographed on silica gel eluting with EtOAc:hexane (1:1)

Sources & evidence

ORD record
ord-4307932ebd8a4da1b776e3c2d4b5a18b
Source dataset
uspto-grants-2008_05
Patent number
US07371767B2

Reaction notes

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