Potassium Carbonate → HCID 57686382, compound

HRID 1038142Notes

Reaction equation

HRID 1038142 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>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].O1CCOCC1.O>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH:20]=[C:21]([C:2]2[S:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6120402-Bromo-1,3-benzothiazoleHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 57686382HCID 57686382, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-bromo-benzothiazole (0.38 g, 1.1 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.5 g, 1.62 mmol), potassium carbonate (0.67 g, 4.85 mmol), Pd(dppf)Cl2 (0.132 g, 0.16 mmol) and 4/1/dioxane/water (10 ml) was degassed for 15 minutes. Then it was heated at 90° C. for overnight. Cooled to room temperature and diluted with EtOAc (200 mL). The organic layer was washed with water (100 ml), dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel to give the desired product 21BB (0.4 g, 78%).

Workup

  1. customwas degassed for 15 minutes
  2. temperatureCooled to room temperature
  3. additiondiluted with EtOAc (200 mL)
  4. washThe organic layer was washed with water (100 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-079ca7fed79c4c67b3260579738cdc85
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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