Cesium carbonate → N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide

HRID 626504

反応式

HRID 626504 の反応式
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH:24]1([C:27]([NH2:29])=[O:28])[CH2:26][CH2:25]1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[N+:15]([C:12]1[N:11]=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:29][C:27]([CH:24]3[CH2:26][CH2:25]3)=[O:28])[CH:7]=2)=[CH:14][CH:13]=1)([O-:17])=[O:16]

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 80376CyclopropanecarboxamideHCID 593227792-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine

生成物 1

HCID 90410505N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide収率 64%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl触媒HCID 312751,4-Dioxane溶媒

実験手順

A suspension of Example A1 (2.00 g, 7.95 mmol), Cs2CO3 (5.00 g, 15.35 mmol), XPhos (0.200 g, 0.420 mmol), Pd2(dba)3 (0.200 g, 0.218 mmol) and cyclopropylcarboxamide (1.00 g, 11.75 mmol) in dioxane (20 mL) was heated at 90° C. under argon overnight. The mixture was cooled to RT and the solids removed via filtration and washed with DCM and THF. The filtrate was concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide (1.52 g, 64%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.01 (s, 1H), 8.57 (dd, J=2.8, 0.5 Hz, 1H), 8.40 (m, 1H), 8.31 (d, J=5.7 Hz, 1H), 7.98 (dd, J=8.9, 2.8 Hz, 1H), 7.85 (d, J=2.4 Hz, 1H), 6.89 (dd, J=5.7, 2.4 Hz, 1H), 1.97 (m, 1H), 0.77 (m, 4H); MS (ESI) m/z: 301.1 (M+H+).

後処理

  1. customthe solids removed via filtration
  2. washwashed with DCM and THF
  3. concentrationThe filtrate was concentrated to dryness
  4. custompurified via silica gel chromatography (EtOAc/Hex)

出典と根拠

ORDレコード
ord-a55ddaf05617467f95bcbe7d49fb3c62
出典データセット
uspto-grants-2016_04
特許番号
US09309224B2

関連ノート

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