5-Bromo-6-methylpyridin-3-amine → 2-Methyl-2'-morpholino-[3,4'-bipyridin]-5-amine

HRID 594067ノート

反応式

HRID 594067 の反応式
Br[C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[N:6][C:7]=1[CH3:8].CC1(C)C(C)(C)OB([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:19]=2)O1>COCCOC.C(=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>[CH3:8][C:7]1[C:2]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[CH:19]=2)=[CH:3][C:4]([NH2:9])=[CH:5][N:6]=1

参加物

6

反応物 2

HCID 184588965-Bromo-6-methylpyridin-3-amineHCID 210816614-(4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine

生成物 1

HCID 904086172-Methyl-2'-morpholino-[3,4'-bipyridin]-5-amine

試薬・触媒・溶媒 3

HCID 178418807HCID 178418807、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 10340Sodium Carbonate溶媒

反応条件

温度
110 °C

実験手順

To a solution of 5-bromo-6-methylpyridin-3-amine (1.0 equiv.) and 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine (1.7 equiv.) in DME and 2M sodium carbonate (4:1, 0.14 M) was added PdCl2(dppf)-DCM adduct (0.1 equiv.) in a microwave vial equipped with a stir bar. The reaction was heated to 110° C. for 15 min in the microwave. The cooled reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried with sodium sulfate, filtered and concentrated. The crude material was purified by flash chromatography over silica gel (DCM with a 0-20% methanol gradient). The pure fractions were concentrated in vacuo to afford 2-methyl-2′-morpholino-[3,4′-bipyridin]-5-amine in quantitative yield. LCMS (m/z) (M+H)=271.1, Rt=0.26 min.

後処理

  1. customvial equipped with a stir bar
  2. customThe cooled reaction mixture
  3. customwas partitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography over silica gel (DCM with a 0-20% methanol gradient)
  8. concentrationThe pure fractions were concentrated in vacuo

出典と根拠

ORDレコード
ord-5054853f24dc45b09b0cf3dbe3fac5f4
出典データセット
uspto-grants-2016_01
特許番号
US09242969B2

反応ノート

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