Potassium Phosphate, Tribasic → HCID 58494034, compound

HRID 1942687Notes

Reaction equation

HRID 1942687 reaction equation
Br[C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH:14]([CH3:16])[CH3:15])=[C:9]([Cl:17])[CH:8]=2)[S:4][N:3]=1.[CH2:18]([C:20]1[C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][CH:23]=[CH:22][C:21]=1[CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)[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[CH:8]=[C:7]([C:5]2[S:4][N:3]=[C:2]([C:25]3[C:20]([CH2:18][CH3:19])=[C:21]([CH:35]4[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]4)[CH:22]=[CH:23][CH:24]=3)[N:6]=2)[CH:12]=[CH:11][C:10]=1[O:13][CH:14]([CH3:16])[CH3:15]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 584940863-Bromo-5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazoleHCID 58494122HCID 58494122, compound

Product 1

HCID 58494034HCID 58494034, compoundYield 23.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazole (D43) (548 mg, 1.643 mmol), 4-[2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperidine (D119) (544 mg, 1.725 mmol) and Pd(Ph3P)4 (190 mg, 0.164 mmol) in N,N-Dimethylformamide (DMF) (5 mL) and Water (1.000 mL) was added tripotassium phosphate (1395 mg, 6.57 mmol), The solution was sealed and irritated in Biotage MW at 120° C. for 20 min. The mixture was directly dried with silica gel and purified by column chromatography to afford 4-[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]piperidine (D122) (169 mg). MS (ES): C24H28ClN3OS requires 441.2. found 442.2 (M+H+).

Workup

  1. customThe solution was sealed
  2. customThe mixture was directly dried with silica gel
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-13f3eff74d874ff981d5449197f2520b
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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