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

HRID 58100
Notes
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Reaction equation

HRID 58100 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]3[C:10]=2[CH:11]=[N:12][NH:13]3)O1.Br[C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:26][C:25]=1[F:34].[C:35](=[O:38])(O)[O-:36].[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>[C:35]([OH:36])([C:18]([F:21])([F:20])[F:19])=[O:38].[F:34][C:25]1[CH:26]=[C:27]([S:30]([NH2:33])(=[O:31])=[O:32])[CH:28]=[CH:29][C:24]=1[C:9]1[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][NH:13]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27784044-Bromo-3-fluorobenzene-1-sulfonamideHCID 897828064-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole

Product 2

HCID 6422Trifluoroacetic acidHCID 897828143-fluoro-4-(6-(trifluoromethyl)-1H-indazol-4-yl)benzenesulfonamideYield 59.6%

Reagents, catalysts & solvents

2
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

To a 5 mL vial equipped with a magnetic stir bar were added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (40 mg, 0.128 mmol), 4-bromo-3-fluorobenzenesulfonamide (39.1 mg, 0.154 mmol), aqueous saturated sodium bicarbonate (0.274 mL, 0.513 mmol), PdCl2(dppf) (9.38 mg, 0.013 mmol), and dioxane (2 mL) to give an orange suspension. The vial was sealed and then heated in a microwave reactor at 140° C. for 30 minutes. The reaction mixture was subsequently filtered and the product was purified by preparative HPLC, eluting with a gradient of 35-60% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA). The pure fractions were lyophilized to give a TFA salt of the title compound as a white solid (13.7 mg, 22.6%). 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 C14H9F4N3O2S, 360.0. found 360.1.

Workup

  1. customTo a 5 mL vial equipped with a magnetic stir bar
  2. customto give an orange suspension
  3. customThe vial was sealed
  4. filtrationThe reaction mixture was subsequently filtered
  5. customthe product was purified by preparative HPLC
  6. washeluting with a gradient of 35-60% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA)

Sources & evidence

ORD record
ord-1af81cde047c419ca4041ba7ffe19fbe
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434743B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes