Sodium Bicarbonate → HCID 89783078, compound

HRID 58081Notes

Reaction equation

HRID 58081 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[C:25]([CH3:31])=[N:26][CH:27]=[CH:28][C:29]=1[NH2:30].[C:32]([O-:35])(O)=[O:33].[Na+]>O1CCOCC1.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]>[C:32]([OH:35])([C:18]([F:21])([F:20])[F:19])=[O:33].[CH3:31][C:25]1[C:24]([C:9]2[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[C:14]3[C:10]=2[CH:11]=[N:12][NH:13]3)=[C:29]([NH2:30])[CH:28]=[CH:27][N:26]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 134195743-Bromo-2-methylpyridin-4-amineHCID 897828064-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole

Product 2

HCID 6422Trifluoroacetic acidHCID 89783078HCID 89783078, compoundYield 13%

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

A vial was charged with a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (0.1 g, 0.320 mmol), 3-bromo-2-methylpyridin-4-amine (0.078 g, 0.417 mmol) and PdCl2(dppf) (0.012 g, 0.016 mmol) in dioxane (8 mL) and aqueous saturated NaHCO3 (2 mL). The resulting light brown suspension was heated at 140° C. for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with 20% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 5 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as clear oil (12 mg, 13%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.11 (s, 3H), 6.69 (br s, 1H), 6.90 (d, J=7.07 Hz, 1H), 7.38 (s, 1H), 8.01 (s, 1H), 8.08 (s, 1H), 8.17 (t, J=6.44 Hz, 1H), 13.51 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H11F3N4, 293.1. found 293.14.

Workup

  1. concentrationThe reaction mixture was subsequently concentrated
  2. customthe crude residue was purified by preparative HPLC
  3. washeluting with 20% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 5 minutes
  4. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-3f8df43941ad462ba358096c49a303e6
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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