Potassium Phosphate, Tribasic → HCID 57522699, compound

HRID 1942619Notes

Reaction equation

HRID 1942619 reaction equation
[Br:1][C:2]1[N:6]=[C:5](Cl)[S:4][N:3]=1.CC1(C)C(C)(C)OB([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Br:1][C:2]1[N:6]=[C:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:24])[CH3:25])=[C:18]([C:26]([F:27])([F:29])[F:28])[CH:17]=2)[S:4][N:3]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27250533-Bromo-5-chloro-1,2,4-thiadiazoleHCID 58494057HCID 58494057, compound

Product 1

HCID 57522699HCID 57522699, compoundYield 52.9%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-bromo-5-chloro-1,2,4-thiadiazole (604 mg), 4,4,5,5-tetramethyl-2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,2-dioxaborolane (D42) (500 mg) and tripotassium phosphate (964 mg) in N,N-dimethylformamide (DMF) (3 mL) and water (0.600 mL) stirred under nitrogen at room temperature was added PdCl2(dppf)-CH2Cl2 adduct (618 mg). The reaction mixture was sealed and heated under microwave at 80° C. for 1 h. The reaction mixture was concentrated and the residue was purified by column chromatography to give 3-bromo-5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,2,4-thiadiazole (D45) (294 mg) as a white solid. MS (ES): C12H10BrF3N2OS requires 366. found 367.2 (M+H+).

Workup

  1. customThe reaction mixture was sealed
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3e89e3c62c174fc7b15c59770be7ebdc
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

Loading…