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

HRID 1028052ノート

反応式

HRID 1028052 の反応式
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]

参加物

5

反応物 2

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

生成物 1

HCID 86656452HCID 86656452、化合物収率 17%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-14ce12aec69f4a8d97f84a7a6fb7e1b8
出典データセット
uspto-grants-2014_05
特許番号
US08735424B2

反応ノート

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