Potassium Carbonate → 7-[3-(3-Furyl)phenoxy]-2,3-dihydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide

HRID 851888Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:20]=[CH:19][C:9]2[N:10]3[CH2:18][CH2:17][CH2:16][C:11]3=[N:12][S:13](=[O:15])(=[O:14])[C:8]=2[CH:7]=1.[O:24]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25]1.C([O-])([O-])=O.[K+].[K+]>C(O)C.O>[O:24]1[CH:28]=[CH:27][C:26]([C:2]2[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=2)[O:5][C:6]2[CH:20]=[CH:19][C:9]3[N:10]4[CH2:18][CH2:17][CH2:16][C:11]4=[N:12][S:13](=[O:15])(=[O:14])[C:8]=3[CH:7]=2)=[CH:25]1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of the product obtained in Step A of Example 16 (300 mg, 0.76 mmol), 111 mg (0.99 mmol) of 3-furanboronic acid, 137 mg (0.99 mmol) of K2CO3 and 45 mg (0.038 mmol) of tetrakistriphenylphosphine in a mixture of 6 ml of ethanol and 1.8 ml of water is heated at 80° C. for 3 hours under N2. The ethanol is evaporated off in vacuo and the residue is taken up in water and 1N HCl. The precipitate is filtered off to yield the title product.

Workup

customThe ethanol is evaporated off in vacuo
filtrationThe precipitate is filtered off

Sources & evidence

ORD record: ord-4bd4b7dab0a24d1ab48e3534a80dc8af
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253163B2

Reaction notes

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