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

HRID 594067노트

반응식

HRID 594067 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 178418807HCID 178418807, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 10340Sodium Carbonate용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5054853f24dc45b09b0cf3dbe3fac5f4
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242969B2

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