Sodium Carbonate → HCID 86718159, compound

HRID 570576Notes

Reaction equation

HRID 570576 reaction equation
Br[C:2]1[N:6]=[C:5]([N:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)[S:4][N:3]=1.[Cl:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+].[ClH:36].O1CCOCC1>COCCOC.O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOCC>[ClH:20].[ClH:36].[Cl:20][C:21]1[CH:26]=[C:25]([C:2]2[N:6]=[C:5]([N:7]3[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]3)[S:4][N:3]=2)[CH:24]=[CH:23][CH:22]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 204431481,4-Dioxane hydrochlorideHCID 71186250HCID 71186250, compound

Product 1

HCID 86718159HCID 86718159, compoundYield 90%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl 4-(3-bromo-1,2,4-thiadiazol-5-yl)piperazine-1-carboxylate (1 g, 2.86 mmol), 3-chlorophenylboronic acid (537 mg, 3.44 mmol), Na2CO3 (364 mg, 3.44 mmol) and tetrakis(triphenylphosphine) palladium (0) (66.2 mg, 57.3 μmol) in 36 mL DME/12 mL water was heated to 100° C. over night. The mixture was extracted with EtOAc (80 mL)/water (80 mL). The organic layer was dried over Na2SO4, filtered off and concentrated in vacuo to give amber oil which was dissolved in 25 mL dioxane, 7.16 mL 4N HCl/dioxane was added and stirred over night at RO. Et2O was added and the mixture was filtered and washed with Et2O. The filter cake was dried in vacuo at 50° C. to yield 926 mg (90%) of the intermediate compound as light yellow solid. MS (m/e): 281.0 (MH+).

Workup

  1. extractionThe mixture was extracted with EtOAc (80 mL)/water (80 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered off
  4. concentrationconcentrated in vacuo
  5. customto give amber oil which
  6. filtrationthe mixture was filtered
  7. washwashed with Et2O
  8. customThe filter cake was dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-0fef3fa7ea4b4aa89e11bf69774ada71
Source dataset
uspto-grants-2015_05
Patent number
US09023852B2

Reaction notes

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