Potassium Phosphate, Tribasic → HCID 58494152, compound

HRID 1942707Notes

Reaction equation

HRID 1942707 reaction equation
[CH2:1]([C:3]1[C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:21][CH2:20]1)[CH3:2].Br[C:32]1[N:36]=[C:35]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH:44]([CH3:46])[CH3:45])=[C:39]([Cl:47])[CH:38]=2)[S:34][N:33]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C.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:47][C:39]1[CH:38]=[C:37]([C:35]2[S:34][N:33]=[C:32]([C:8]3[C:3]([CH2:1][CH3:2])=[C:4]([CH2:18][CH:19]4[CH2:20][CH2:21][N:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:23][CH2:24]4)[CH:5]=[CH:6][CH:7]=3)[N:36]=2)[CH:42]=[CH:41][C:40]=1[O:43][CH:44]([CH3:45])[CH3:46]

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 584940863-Bromo-5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazoleHCID 58494160HCID 58494160, compound

Product 1

HCID 58494152HCID 58494152, compoundYield 30.7%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl (4-{[2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}-1-piperidinyl)acetate (D144) (200 mg, 0.481 mmol), 3-bromo-5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazole (D43) (161 mg, 0.481 mmol), tripotassium phosphate (307 mg, 1.444 mmol) and Pd(Ph3P)4 (55.6 mg, 0.048 mmol) in N,N-Dimethylformamide (DMF) (6 mL) and Water (1.500 mL) was heated by Biotage Initiator to 120° C. for 15 min. The reaction solution was diluted with ethyl acetate, washed with water, dried over sodium sulphate, concentrated and purified by ISCO column chromatography to afford ethyl (4-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]methyl}-1-piperidinyl)acetate (D145) (80 mg). MS (ES): C29H36ClN3O3S requires 541.2. found 542.2 (M+H+).

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated
  4. custompurified by ISCO column chromatography

Sources & evidence

ORD record
ord-bc30833c215f489b9c1baae0f229f0fe
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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