Potassium Carbonate → HCID 66868666, compound

HRID 68587Notes

Reaction equation

HRID 68587 reaction equation
Br[C:2]1[CH:16]=[C:15]([CH2:17][N:18]([CH3:29])[S:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[C:30]([C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)#[N:31].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:30]([C:32]1[CH:37]=[C:36]([C:2]2[CH:16]=[C:15]([CH2:17][N:18]([CH3:29])[S:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:14]=[CH:13][C:3]=2[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH:35]=[CH:34][CH:33]=1)#[N:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 66868198HCID 66868198, compound

Product 1

HCID 66868666HCID 66868666, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a DMF (50 mL) solution of t-butyl 2-(2-bromo-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate (3) (1.25 g, 2.6 mmol, 1 eq) was added 3-cyanobenzeneboronic acid (0.57 g, 3.8 mmol, 1.5 eq, Frontier Scientific, Inc., Logan, Utah, USA), potassium carbonate (1 g, 7.7 mmol, 3 eq), and tetrakis(triphenylphoshine)palladium (0.15 g, 0.13 mmol, 0.05 eq). The mixture was stirred at 90° C. for 18 h. After concentration in vacuo, the residue was extracted between EtOAc (100 ml) and brine (100 mL). The separated EtOAc layer was dried (Na2SO4), concentrated and purified via silica gel chromatography (linear gradient of 0% EtOAc/hexanes to 100% EtOAc/hexanes) to yield 0.78 g (59.8%) of t-butyl 2-(2-(3-cyanophenyl)-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate (4). 1HNMR (CDCl3, 300 MHz): δ 7.80 (m, 4H), 7.58 (m, 1H), 7.48 (t, 1H), 7.21 (m, 4H), 6.79 (d, 1H), 4.52 (s, 2H), 4.11 (s, 2H), 2.61 (s, 3H), 1.45 (s, 9H).

Workup

  1. concentrationAfter concentration in vacuo
  2. extractionthe residue was extracted between EtOAc (100 ml) and brine (100 mL)
  3. dry with materialThe separated EtOAc layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via silica gel chromatography (linear gradient of 0% EtOAc/hexanes to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-56e51b60e1e64fb0aa0dc82e8f58a4dd
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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