Potassium Carbonate → HCID 70981429, compound

HRID 1468677Notes

Reaction equation

HRID 1468677 reaction equation
Br[C:2]1[C:10]2[S:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([CH3:11])[C:3]=1[OH:12].[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.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:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[C:10]3[S:9][CH:8]=[N:7][C:6]=3[CH:5]=[C:4]([CH3:11])[C:3]=2[OH:12])=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 70981708HCID 70981708, compound

Product 1

HCID 70981429HCID 70981429, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

The reaction mixture of 7-bromo-5-methylbenzo[d]thiazol-6-ol (5D) (90 mg, 0.37 mmol), 4-chlorophenyl boronic acid (86 mg, 0.55 mmol), Pd(PPh3)4 (40 mg, 0.037 mmol), K2CO3 (153 mg, 1.11 mmol) in 1,2-dimethoxyethane (1 ml)/H2O(0.5 ml) was heated at 110° C. in the microwave for 10 min. Then the reaction mixture was diluted with water, extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, concentrated and purified by silica gel column (0-100% ethyl acetate/hexanes). LCMS-ESI+: calc'd for C14H10ClNOS: 276.0 (M+H+). Found: 276.2 (M+H+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel column (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4e44ca570734415289f9cb8bb616c8f2
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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