Potassium Carbonate → HCID 59192625, compound

HRID 1696885Notes

Reaction equation

HRID 1696885 reaction equation
[C:1]([O:5][C:6](=[O:30])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH:14]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[F:37][C:38]1[CH:43]=[CH:42][N:41]=[C:40](B(O)O)[CH:39]=1>O1CCOCC1.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>[C:1]([O:5][C:6](=[O:30])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH:14]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([C:40]4[CH:39]=[C:38]([F:37])[CH:43]=[CH:42][N:41]=4)=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 17750492(4-Fluoropyridin-2-yl)boronic acidHCID 59192605HCID 59192605, compound

Product 1

HCID 59192625HCID 59192625, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a degassed, stirred mixture of [5-(4-bromo-benzenesulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester (150 mg, 0.30 mmol) in 1,4-dioxane (10 mL) and a 1 M aqueous solution of potassium carbonate (0.89 mL, 0.89 mmol) was added 4-fluoro-pyridine-2-boronic acid (51 mg, 0.36 mmol) and tetrakis(triphenylphosphine)palladium(0) (16 mg, 0.014 mmol) under argon at room temperature. The mixture was heated at reflux for 4 hours. After being cooled to room temperature, the solvents were removed under reduced pressure. The crude residue was diluted with ethyl acetate (50 mL), washed with water (10 mL×2), dried over anhydrous sodium sulfate, and concentrated in vacuo to give crude {5-[4-(4-fluoro-pyridin-2-yl)-benzenesulfonylamino]-5,6,7,8-tetrahydro-naphthalen-1-yloxy}-acetic acid tert-butyl ester, which was used without further purification. MS cald. for C27H29FN2O5S 512, obsd. 513 [(M+H)+].

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 hours
  3. customthe solvents were removed under reduced pressure
  4. additionThe crude residue was diluted with ethyl acetate (50 mL)
  5. washwashed with water (10 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39cdb5adaa854bc0a26bccf934cdba9c
Source dataset
uspto-grants-2012_04
Patent number
US08163781B2

Reaction notes

Loading…