Potassium Carbonate → HCID 58924800, compound

HRID 1991001Notes

Reaction equation

HRID 1991001 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([N:9]2[CH:14]([CH3:15])[CH2:13][CH2:12][CH2:11][CH:10]2[CH3:16])=[O:8])[N:6]=1.[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:16][CH:10]1[CH2:11][CH2:12][CH2:13][CH:14]([CH3:15])[N:9]1[C:7]([C:5]1[N:6]=[C:2]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH3:17])[S:3][CH:4]=1)=[O:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 58924881HCID 58924881, compound

Product 1

HCID 58924800HCID 58924800, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture containing (2-bromo-thiazol-4-yl)-(2,6-dimethyl-piperidin-1-yl)-methanone (Step 1; 91 mg, 0.3 mmol), 2-methylphenylboronic acid (45 mg, 0.33 mmol), Pd(dppf)Cl2 (Dichloro-(1,1-bis(diphenylphosphino)-ferrocene) palladium(II)) (11 mg, 0.015 mmol), and potassium carbonate (0.3 mL, 2 M aqueous, 0.6 mmol) in DME (2 mL) was heated to 90° C. for 8 hrs. The solvent was evaporated and water (5 mL) was added. The mixture was extracted with ethyl acetate (3×5 mL). The combined organic layers were dried with MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography with a solvent gradient of 0-30% ethyl acetate in hexanes to give (2,6-dimethyl-piperidin-1-yl)-(2-o-tolyl-thiazol-4-yl)-methanone (68 mg, 75%) as a white solid.

Workup

  1. customThe solvent was evaporated
  2. additionwater (5 mL) was added
  3. extractionThe mixture was extracted with ethyl acetate (3×5 mL)
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography with a solvent gradient of 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-04be294015b3460188259d98bb362748
Source dataset
uspto-grants-2010_01
Patent number
US07645773B2

Reaction notes

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