Sodium Bicarbonate → HCID 89783820, compound

HRID 58101Notes

Reaction equation

HRID 58101 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:25]=[CH:26][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[N:28][CH:29]=1.[C:34](=[O:37])(O)[O-:35].[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:34]([OH:35])([C:18]([F:21])([F:20])[F:19])=[O:37].[F:21][C:18]([F:19])([F:20])[C:16]1[CH:15]=[C:14]2[C:10]([CH:11]=[N:12][NH:13]2)=[C:9]([C:24]2[CH:25]=[CH:26][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[N:28][CH:29]=2)[CH:17]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 509897865-Bromopyridine-2-sulfonamideHCID 897828064-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole

Product 2

HCID 6422Trifluoroacetic acidHCID 89783820HCID 89783820, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (39.5 mg, 0.127 mmol), 5-bromopyridine-2-sulfonamide (45 mg, 0.190 mmol), PdCl2(dppf) (9.26 mg, 0.013 mmol), sodium bicarbonate (0.271 mL, 0.506 mmol), and dioxane (2 mL) 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 35-60% 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 (9.9 mg, 17%). 1H NMR (400 MHz, CD3OD) δ ppm 2.01 (s, 1H), 7.61 (d, J=1.26 Hz, 1H), 8.03 (s, 1H), 8.17-8.21 (m, 1H), 8.34 (d, J=1.01 Hz, 1H), 8.43 (dd, J=8.08, 2.27 Hz, 1H), 9.07 (dd, J=2.27, 0.76 Hz, 1H); ESI-MS m/z [M+H]+ calc'd for C13H9F3N4O2S, 343.0. found 343.2.

Workup

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

Sources & evidence

ORD record
ord-319d032c7f8a4668a42417d06683a2a5
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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