Sodium Carbonate → 5-(6-Methoxy-benzothiazol-2-yl)-thiophene-2-carboxylic acid

HRID 579455Notes

Reaction equation

Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:13]([C:16]1[S:17][C:18](B(O)O)=[CH:19][CH:20]=1)([OH:15])=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>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>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:18]3[S:17][C:16]([C:13]([OH:15])=[O:14])=[CH:20][CH:19]=3)[S:3][C:4]=2[CH:10]=1

Participants

Conditions

Temperature: 120 °C

Procedure

2-Bromo-6-methoxy-benzothiazole (1.22 g, 5.00 mmol), 2-carboxythiophene-5-boronic acid (860 mg, 5.00 mmol), sodium carbonate (2.65 g, 25.00 mmol) and tetrakis(triphenylphosphine)palladium (300 mg, 0.25 mmol) were dissolved in a mixture of 80 mL N,N-dimethylformamide and 80 mL water. The mixture was stirred at 120° C. under argon for 2 h. The reaction mixture was evaporated and the residue was partitioned between 100 mL of water and 100 mL of dichloromethane. A considerable amount of white solid precipitated between the layers and was filtered off and triturated with diethyl ether, affording the title compound (550 mg, 1.89 mmol, 38%) as a white powder.

Workup

customThe reaction mixture was evaporated
customthe residue was partitioned between 100 mL of water and 100 mL of dichloromethane
customA considerable amount of white solid precipitated between the layers
filtrationwas filtered off
customtriturated with diethyl ether

Sources & evidence

ORD record: ord-3b8a9b163e4944ffac70392f51174513
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040714B2

Reaction notes

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