Sodium Carbonate → 3-(4-(4-aminopyridin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)benzenesulfonamide

HRID 1186825Notes

Reaction equation

HRID 1186825 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:11]3[CH:12]=[C:13]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:9]=[CH:10][C:3]=12.[NH2:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][C:23]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCO.COCCOC.O>[NH2:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][C:23]=1[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:11]3[CH:12]=[C:13]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:9]=[CH:10][C:3]=12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 23583877(4-Aminopyridin-3-yl)boronic acidHCID 666648613-(4-iodo-1H-pyrazolo[3,4-b]pyridin-1-yl)benzenesulfonamide

Product 1

HCID 666684103-(4-(4-aminopyridin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)benzenesulfonamideYield 33.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
105 °C

Procedure

Example 79 was prepared according to the general procedure in Example 2, except heating at 105° C. for 2.25 h, and using the following materials: Intermediate 1A (50 mg, 0.084 mmol), 4-aminopyridin-3-ylboronic acid (81 mg, 0.59 mmol), sodium carbonate (31 mg, 0.292 mmol), EtOH:DME:H2O (1.2:2.5:1.0 ratio) (1.5 mL) and tetrakis(triphenylphosphine)palladium(0) (9.65 mg, 8.35 μmol). Example 79 was isolated as a yellow solid (10.2 mg, 32.3%). Purification was done by preparative HPLC (Condition A) using a Phenomenex Luna Axia 30×100 mm S10 column from 5% Solvent B to 85% Solvent B over 12 min, ret. T=5.7 min. 1H NMR (500 MHz, METHANOL-d4) δ ppm 8.93-9.00 (1 H, m), 8.71-8.79 (1 H, m), 8.60-8.67 (1 H, m), 8.22-8.27 (1 H, m), 8.18 (1 H, s), 8.09-8.14 (1 H, m), 7.84-7.93 (1 H, m), 7.69-7.80 (1 H, m), 7.37-7.47 (1 H, m), 6.79-6.92 (1 H, m) LC/MS (Condition B): ret. T=1.75 min, (M+H)+ 366.98. Analytical HPLC: (Condition A): >97%, ret. T=13.51 min, (Condition B): >97%, ret. T=15.81 min, (Condition C): >99%, ret. T=4.54 min, (Condition D): >97%, ret. T=4.87 min.

Workup

  1. customExample 79 was prepared

Sources & evidence

ORD record
ord-56f5cfcefea84cedb71cb74935f05e12
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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