Sodium Bicarbonate → 3-(6-(trifluoromethyl)-1H-indazol-4-yl)benzenesulfonamide

HRID 58098Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[S:15]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)(=[O:18])(=[O:17])[NH2:16].C(=O)(O)[O-].[Na+]>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].O1CCOCC1>[F:12][C:11]([F:14])([F:13])[C:9]1[CH:8]=[C:7]2[C:3]([CH:4]=[N:5][NH:6]2)=[C:2]([C:23]2[CH:24]=[C:19]([S:15]([NH2:16])(=[O:18])=[O:17])[CH:20]=[CH:21][CH:22]=2)[CH:10]=1

Participants

Conditions

Temperature: 140 °C

Procedure

4-Bromo-6-(trifluoromethyl)-1H-indazole (40 mg, 0.151 mmol), (3-sulfamoylphenyl)boronic acid (45.5 mg, 0.226 mmol), PdCl2(dppf) (11.04 mg, 0.015 mmol), sodium bicarbonate (323 μL, 0.604 mmol), and dioxane were mixed in a 10 mL vial to give an orange suspension. The vial was sealed and then heated to 140° C. for 20 minutes in a microwave reactor. The reaction mixture was subsequently filtered and the product was purified by preparative HPLC, eluting with a gradient of 35-70% ACN in H2O (containing 10 mM NH4HCO3). The pure fractions were lyophilized to give the title compound as a white solid (35.8 mg, 69.5%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.50 (s, 2H), 7.53 (s, 1H), 7.75-7.80 (m, 1H), 7.92-7.94 (m, 1H), 8.02 (s, 1H), 8.06 (dt, J=8.02, 1.29 Hz, 1H), 8.21 (t, J=1.64 Hz, 1H), 8.40 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H10F3N3O2S, 342.0. found 342.2.

Workup

customto give an orange suspension
customThe vial was sealed
filtrationThe reaction mixture was subsequently filtered
customthe product was purified by preparative HPLC
washeluting with a gradient of 35-70% ACN in H2O (containing 10 mM NH4HCO3)

Sources & evidence

ORD record: ord-367f38fb34bc4b4e8d6789a8dc992bd1
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434743B2

Reaction notes

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