Potassium Carbonate → HCID 66835664, compound

HRID 2404437Notes

Reaction equation

HRID 2404437 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.[B-](F)(F)(F)[CH2:60][CH2:61][C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63].[K+].C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1.O>[C:65]([O:64][C:62](=[O:63])[CH2:61][CH2:60][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[CH:3]=1)([CH3:68])([CH3:67])[CH3:66]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylHCID 49761675Potassium (3-tert-butoxy-3-oxopropyl)(trifluoro)borate(1-)HCID 66835733HCID 66835733, compound

Product 1

HCID 66835664HCID 66835664, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A screw-cap tube is charged with 2-[(3-bromophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole (208 mg), palladium(II) acetate (3 mg), RuPhos® 6 (12 mg), potassium 3-trifluoroboratopropionate tert-butyl ester (118 mg), potassium carbonate (207 mg), water (2.5 mL) and toluene (2.5 mL). The tube is evacuated, filled with argon and sealed. After stirring at 120° C. overnight, the mixture is diluted with ethyl acetate and water and the aqueous phase is extracted with ethyl acetate. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol from 100/0 to 95/5) to afford 3-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}propionic acid tert-butyl ester.

Workup

  1. customThe tube is evacuated
  2. additionfilled with argon
  3. customsealed
  4. additionthe mixture is diluted with ethyl acetate and water
  5. extractionthe aqueous phase is extracted with ethyl acetate
  6. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by chromatography (gradient dichloromethane/methanol from 100/0 to 95/5)

Sources & evidence

ORD record
ord-9ef0ce0cb51148bbb2c15820de670fd0
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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