Sodium Sulfate → HCID 56597563, compound

HRID 1522393Notes

Reaction equation

HRID 1522393 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.[CH3:27][O:28][C:29]1[CH:30]=[N:31][CH:32]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:34]=1.C(=O)(O)[O-].[Na+].[O-]S([O-])(=O)=O.[Na+].[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].C(Cl)Cl.O.COCCOC>[CH3:24][C:23]1[CH:22]=[C:21]([CH3:25])[NH:20][C:19](=[O:26])[C:18]=1[CH2:17][NH:16][C:14]([C:4]1[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=[C:2]([C:33]2[CH:32]=[N:31][CH:30]=[C:29]([O:28][CH3:27])[CH:34]=2)[CH:3]=1)=[O:15]

Participants

8

Reactant 4

HCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 38661613-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 565974256-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Product 1

HCID 56597563HCID 56597563, compound

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a 20 mL microwave vial were sequentially added 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (100 mg, 0.267 mmol, 3-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (69.2 mg, 0.294 mmol), PdCl2(dppf)-CH2Cl2 adduct (21.84 mg, 0.027 mmol), (DME) (5 mL), and water (2 mL). The reaction mixture was degassed with nitrogen for 5 min. Sodium bicarbonate (67.4 mg, 0.802 mmol) was added and the contents sealed and irradiated (microwave) at 140° C. The reaction mixture was cooled to room temperature and poured on a silica column (through Na2SO4) and purified by silica gel chromatography (eluent: 5% MeOH/CH2Cl2) which provided the desired product as an off-white solid after preciptation from EtOAc/MeOH. The final product was collected as 0.090 g (76%). LCMS E-S (M+H) 447.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.57 (s., 1 H), 9.06 (d, J=1.52 Hz, 1 H), 8.92-9.00 (m, 1 H), 8.39-8.48 (m, 2 H), 8.24 (s, 1 H), 8.14 (d, J=1.77 Hz, 1 H), 5.91 (s, 1 H), 5.30-5.45 (m, 1 H), 4.42 (d, J=4.80 Hz, 2 H), 3.97 (s, 3 H), 2.24 (s, 3 H), 2.13 (s, 3 H), 1.55 (d, J=6.82 Hz, 6 H).

Workup

  1. customThe reaction mixture was degassed with nitrogen for 5 min
  2. customthe contents sealed
  3. customirradiated (microwave) at 140° C
  4. custompurified by silica gel chromatography (eluent: 5% MeOH/CH2Cl2) which

Sources & evidence

ORD record
ord-4928168bcbc940f3bbdf531ae4fb3d49
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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