Potassium Carbonate → HCID 22144506, compound

HRID 1824802Notes

Reaction equation

HRID 1824802 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=3Br)[S:9][C:5]=2[CH:4]=1.[C:21](=O)([O-])[O-].[K+].[K+].CB(O)O>C1(C)C=CC=CC=1.C(OC(=O)C)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>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=3[CH3:21])[S:9][C:5]=2[CH:4]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 22144554HCID 22144554, compound

Product 1

HCID 22144506HCID 22144506, compoundYield 63.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-methoxy-2-(2-bromo-3-methoxy-phenyl)-benzothiazole (0.128, 0.366 mmol) in dry toluene (4 mL) was added potassium carbonate (0.404 g, 2.92 mmol), methylboronic acid (88 mg, 1.47 mmol) and tetrakis(triphenylphosphine)palladium (42 mg, 0.036 mmol). The mixture was heated to 100° C. for 3 h, then cooled to room temperature. The mixture was diluted with ethylacetate and washed with water, saturated sodium carbonate and brine. After chromatographic purification gave 6-methoxy-2-(2-methyl-3-methoxy-phenyl)-benzothiazole (66 mg, 63% yield) as a white solid. Mass spec: MH+=286.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with water, saturated sodium carbonate and brine
  3. customAfter chromatographic purification

Sources & evidence

ORD record
ord-af01ebad47284611a502657edd4f8ff8
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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