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Cesium carbonate → 3-(6-(3-(4-fluorophenoxy)azetidin-1-yl)pyridin-2-ylamino)-N-methylbenzamide

HRID 522922
ノート
印刷プレビュー

反応式

HRID 522922 の反応式
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:11][CH:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH2:9]2)[N:3]=1.N[C:21]1[CH:30]=[CH:29][C:24]([C:25]([NH:27][CH3:28])=[O:26])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([N:86](C)C)=O>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]>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH:10]2[CH2:11][N:8]([C:4]3[N:3]=[C:2]([NH:86][C:22]4[CH:23]=[C:24]([CH:29]=[CH:30][CH:21]=4)[C:25]([NH:27][CH3:28])=[O:26])[CH:7]=[CH:6][CH:5]=3)[CH2:9]2)=[CH:14][CH:15]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 2355164-Amino-N-methylbenzamideHCID 634876Binap, (A+-)-HCID 866852582-Chloro-6-(3-(4-fluorophenoxy)azetidin-1-yl)pyridine

生成物 1

HCID 673555953-(6-(3-(4-fluorophenoxy)azetidin-1-yl)pyridin-2-ylamino)-N-methylbenzamide
収率 13%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
120 °C

実験手順

To a solution of 2-chloro-6-(3-(4-fluorophenoxy) azetidin-1-yl)pyridine (500 mg, 1.79 mmoL) and 4-amino-N-methylbenzamide (270 mg, 1.79 mmol) in dimethylacetamide (5 mL, 3 mL/mmol) was added cesium carbonate (873 mg, 2.68 mmol) and the reaction was degassed for 15 min. Pd2(dba)3 (81 mg, 0.089 mmol) and BINAP (55 mg, 0.089 mmol) were added and the reaction was allowed to heat at 120° C. in the microwave. The reaction was quenched with water and extracted with EtOAc (2×50 mL). The organic extracts were washed with brine, dried over sodium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography to afford 3-(6-(3-(4-fluorophenoxy) azetidin-1-yl)pyridin-2-ylamino)-N-methylbenzamide (61 mg, 13%) as a solid. Observed mass (M+1): 393.1. The following compounds were prepared as described in Example V above using appropriate starting materials.

後処理

  1. customthe reaction was degassed for 15 min
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-eee1e11f6b46466aa9bba959a9aea0bb
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09334269B2

反応ノート

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