Sodium Carbonate → HCID 58942262, compound

HRID 2092286Notes

Reaction equation

HRID 2092286 reaction equation
I[C:2]1[C:3]([CH3:13])=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[N:8]=[C:7]2[NH2:12].[CH3:14][NH:15][C:16]1[N:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21](B3OC(C)(C)C(C)(C)O3)[CH:22]=2)[N:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:12][C:7]1[C:6]2[C:10](=[C:2]([C:21]3[CH:22]=[C:23]4[C:18](=[CH:19][CH:20]=3)[N:17]=[C:16]([NH:15][CH3:14])[N:25]=[CH:24]4)[C:3]([CH3:13])=[CH:4][CH:5]=2)[N:9]([CH3:11])[N:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 16086139N-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)quinazolin-2-amineHCID 58466459HCID 58466459, compound

Product 1

HCID 58942262HCID 58942262, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 7-iodo-1,6-dimethyl-1H-indazol-3-amine (266 mg, 927 μmol), N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine (317 mg, 1112 μmol), sodium carbonate (2 M aqueous) (927 μl, 1853 μmol) and tetrakis(triphenylphosphine)palladium (0) (54 mg, 46 μmol) in dioxane (4 mL) was purged with nitrogen in a sealed microwave vial. The mixture was heated in a microwave reactor at 150° C. for 33 min. Sovent was removed in vacuo and the residue was purified by flash chromatography (1-5% MeOH/DCM) to give the title compound (230 mg, 78%). MS (M+H)+ 319.

Workup

  1. customwas purged with nitrogen in a sealed microwave vial
  2. customSovent was removed in vacuo
  3. customthe residue was purified by flash chromatography (1-5% MeOH/DCM)

Sources & evidence

ORD record
ord-a3ad2a0fe993414b915564a09027a4e9
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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