Water → HCID 70882505, compound

HRID 2234982Notes

Reaction equation

HRID 2234982 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[N:17]=[C:16]([N:18]3[CH2:23][C@H:22]([CH3:24])[N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:20]([CH3:32])[CH2:19]3)[CH:15]=[CH:14][C:13]=2[O:33][CH3:34])(=[O:10])=[O:9])=[C:4]([Cl:35])[CH:3]=1.[CH3:36][C:37]1[S:41][C:40](B(O)O)=[CH:39][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C(OCC)(=O)C>[Cl:35][C:4]1[CH:3]=[C:2]([C:40]2[S:41][C:37]([CH3:36])=[CH:38][CH:39]=2)[CH:7]=[CH:6][C:5]=1[S:8]([NH:11][C:12]1[N:17]=[C:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:20]([CH3:32])[CH2:19]2)[CH:15]=[CH:14][C:13]=1[O:33][CH3:34])(=[O:10])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734374(5-Methylthiophen-2-yl)boronic acidHCID 70882502HCID 70882502, compound

Product 1

HCID 70882505HCID 70882505, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,1-Dimethylethyl (2R,6S)-4-[6-{[(4-bromo-2-chlorophenyl)sulfonyl]amino}-5-(methyloxy)-2-pyridinyl]-2,6-dimethyl-1-piperazinecarboxylate (D13) (0.10 g, 0.169 mmol), 5-methylthiophen-2-boronic acid (0.0739 g, 0.254 mmol), Palladium dichloride di-triphenylphosphine (5.9 mg, 0.0127 mmol), sodium carbonate (0.0359 g, 0.339 mmol) were heated in DME (1 mL) and water (0.5 mL) at 120° C. in the microwave for 20 minutes. The reaction was then diluted with ethyl acetate (50 mL) and washed with saturated sodium hydrogen carbonate (2×30 mL) and brine (30 mL). The organic layer was dried (MgSO4) and evaporated to give a yellow foam which was purified by chromatography [silica gel, eluting with 0 to 70% Ethyl acetate/pentane]. Product fractions evaporated to give a pale yellow oil (D16) (0.088 g) MS (ES+) m/e 607/609 [M+H]+.

Workup

  1. washwashed with saturated sodium hydrogen carbonate (2×30 mL) and brine (30 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customto give a yellow foam which
  5. customwas purified by chromatography [silica gel, eluting with 0 to 70% Ethyl acetate/pentane]
  6. customProduct fractions evaporated

Sources & evidence

ORD record
ord-97c7c1778e4946ce836f816482d55278
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

Loading…