6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → HCID 86656452, compound

HRID 1028052Notes

Reaction equation

HRID 1028052 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][N:13]=[C:14]([Cl:17])[CH:15]=2)[N:10]=[CH:9][CH:8]=1)(=O)=O.[CH3:20][C:21]1[N:26]=[C:25]([NH2:27])[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=1>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.COCCOC>[C:16]([C:24]1[C:25]([NH2:27])=[N:26][C:21]([CH3:20])=[CH:22][C:23]=1[C:7]1[C:16]2[C:11](=[CH:12][N:13]=[C:14]([Cl:17])[CH:15]=2)[N:10]=[CH:9][CH:8]=1)([CH3:11])([CH3:7])[CH3:15]

Participants

5

Reactant 2

HCID 583875776-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 58387621HCID 58387621, compound

Product 1

HCID 86656452HCID 86656452, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 6-chloro-1,7-naphthyridin-4-yl trifluoromethanesulfonate (1.0 equiv.), 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (1.0 equiv.) and Pd(dppf)Cl2—CH2Cl2 (0.1 equiv.) in 3:1 DME/2M Na2CO3 was heated in a microwave at 100° C. for 15 minutes. Upon cooling, the solution was partitioned between EtOAc and Na2CO3(sat.) washed further with NaCl(sat.), dried over MgSO4, concentrated and purified by silica gel chromatography (2-4% MeOH/CH2Cl2 w/0.1% DIEA eluant) to yield tert-butyl 4-(6-chloro-1,7-naphthyridin-4-yl)-6-methylpyridin-2-amine (17%). LC/MS=271.0 (M+H), LC=1.81 min.

Workup

  1. temperatureUpon cooling
  2. customthe solution was partitioned between EtOAc and Na2CO3(sat.)
  3. washwashed further with NaCl(sat.)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (2-4% MeOH/CH2Cl2 w/0.1% DIEA eluant)

Sources & evidence

ORD record
ord-14ce12aec69f4a8d97f84a7a6fb7e1b8
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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