Potassium Carbonate → HCID 66868549, compound

HRID 68591Notes

Reaction equation

HRID 68591 reaction equation
Br[C:2]1[CH:16]=[C:15]([CH2:17][NH:18][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:29]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)#[N:30].C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1.O>[C:29]([C:31]1[CH:36]=[C:35]([C:2]2[CH:16]=[C:15]([CH2:17][NH:18][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:34]=[CH:33][CH:32]=1)#[N:30]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 66869000t-Butyl 2-(2-bromo-4-((4-fluorophenylsulfonamido)methyl)phenoxy)acetate

Product 1

HCID 66868549HCID 66868549, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

t-butyl 2-(2-bromo-4-((4-fluorophenylsulfonamido)methyl)phenoxy)acetate (7) (64 mg, 0.135 mm ol, 1 eq), 3-cyanophenylboronic acid (30 mg, 0.20 mmol, 1.5 eq), K2CO3 (75 mg, 0.54 mmol, 4 eq), Pd(PPh3)4 (2.3 mg, 0.001 mmol, 0.01 eq) and 4 mL of dioxane/H2O (4:1) were heated to 140° C. for 1 h in a microwave. The mixture was then cooled to room temperature, filtered, concentrated in vacuo, and purified by preparative TLC to give 51 mg (76%) of t-butyl 2-(2-(3-cyanophenyl)-4-((4-fluorophenylsulfonamido)methyl)phenoxy)acetate (8).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. custompurified by preparative TLC

Sources & evidence

ORD record
ord-bda38b3b3e7e42a093dc077b6dc86783
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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