Potassium Phosphate, Tribasic → HCID 66981792, compound

HRID 1942677Notes

Reaction equation

HRID 1942677 reaction equation
Br[C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[C:9]([Cl:17])[C:10]([O:13][CH:14]([CH3:16])[CH3:15])=[N:11][CH:12]=2)[S:4][N:3]=1.[CH2:18]([C:20]1[C:25](/[CH:26]=[CH:27]/[O:28][CH3:29])=[CH:24][CH:23]=[CH:22][C:21]=1B1OC(C)(C)C(C)(C)O1)[CH3:19].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.O.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>[Cl:17][C:9]1[C:10]([O:13][CH:14]([CH3:16])[CH3:15])=[N:11][CH:12]=[C:7]([C:5]2[S:4][N:3]=[C:2]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25](/[CH:26]=[CH:27]/[O:28][CH3:29])[C:20]=3[CH2:18][CH3:19])[N:6]=2)[CH:8]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 58494110Pyridine, 5-(3-bromo-1,2,4-thiadiazol-5-yl)-3-chloro-2-(1-methylethoxy)-HCID 669817762-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 66981792HCID 66981792, compoundYield 123.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-(3-bromo-1,2,4-thiadiazol-5-yl)-3-chloro-2-[(1-methylethyl)oxy]pyridine (D109) (1.3 g, 3.89 mmol), 2-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.239 g, 7.77 mmol), tripotassium phosphate (2.474 g, 11.66 mmol) and Pd(Ph3P)4 (0.449 g, 0.389 mmol) in N,N-Dimethylformamide (DMF) (5 mL) and Water (5.00 mL) were heated by Biotage Initiator to 120° C. for 30 min. The reaction solution was concentrated and the slurry was diluted with ethyl acetate, washed with water, dried and purified by ISCO column chromatography to afford 3-chloro-5-(3-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,2,4-thiadiazol-5-yl)-2-[(1-methylethyl)oxy]pyridine (D110) (2 g). MS (ES): C21H22ClN3O2S requires 415.1. found 416.1 (M+H+).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionthe slurry was diluted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. custompurified by ISCO column chromatography

Sources & evidence

ORD record
ord-545b330fd2f045189feb893dfaf050b5
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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