N-(4-(3-(2,3-Dihydrofuran-2-YL)pyridin-2-yloxy)phenyl)pyridin-2-amine → N-(4-(3-(Tetrahydrofuran-2-YL)pyridin-2-yloxy)phenyl)pyridin-2-amine

HRID 473662ノート

反応式

HRID 473662 の反応式
[O:1]1[CH:5]=[CH:4][CH2:3][CH:2]1[C:6]1[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:15][CH:14]=2)=[N:8][CH:9]=[CH:10][CH:11]=1>[Pd].C(O)C>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:15][CH:14]=2)=[N:8][CH:9]=[CH:10][CH:11]=1

参加物

4

反応物 1

HCID 59374334N-(4-(3-(2,3-Dihydrofuran-2-YL)pyridin-2-yloxy)phenyl)pyridin-2-amine

生成物 1

HCID 59374242N-(4-(3-(Tetrahydrofuran-2-YL)pyridin-2-yloxy)phenyl)pyridin-2-amine

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

To a 150 mL round bottom flask was added N-(4-(3-(2,3-dihydrofuran-2-yl)pyridin-2-yloxy)phenyl)pyridin-2-amine (660 mg, 1.992 mmol) and ethanol (7967 μL) before adding palladium, 10% wt. on activated carbon (70 mg, 0.658 mmol) portionwise. The flask was evacuated and backfilled with hydrogen under atmospheric pressure before allowing to stir at room temperature under hydrogen. The reaction was complete after 3 h. After dilution with ethyl acetate, the black suspension was filtered through a pad of Celite while rinsing with ethyl acetate (3×25 mL) before concentrating to a pale yellow residue. The residue was taken up in 5 mL DCM and applied directly to silica for purification (0 to 50% ethyl acetate/hexanes over 35 minutes). The target compound was isolated as a white solid. MS (ESI, pos. ion) m/z: 334.2 (M+1). IC50 (uM) 0.225.

後処理

  1. customThe flask was evacuated
  2. filtrationAfter dilution with ethyl acetate, the black suspension was filtered through a pad of Celite
  3. washwhile rinsing with ethyl acetate (3×25 mL)
  4. concentrationbefore concentrating to a pale yellow residue
  5. customapplied directly to silica for purification (0 to 50% ethyl acetate/hexanes over 35 minutes)
  6. customThe target compound was isolated as a white solid

出典と根拠

ORDレコード
ord-e4d0120a7f3940919a6f00aaa8c9b35c
出典データセット
uspto-grants-2014_01
特許番号
US08637500B2

反応ノート

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