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Cesium carbonate → 3-((5-fluoro-2-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidin-4-yl)amino)-N-methylbenzamide

HRID 522934
ノート
印刷プレビュー

反応式

HRID 522934 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([NH:14][CH3:15])=[O:13])[C:5]([F:19])=[CH:4][N:3]=1.[F:20][C:21]1[CH:31]=[CH:30][C:24]([O:25][CH:26]2[CH2:29][NH:28][CH2:27]2)=[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(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:5]1[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([NH:14][CH3:15])=[O:13])=[N:7][C:2]([N:28]2[CH2:29][CH:26]([O:25][C:24]3[CH:23]=[CH:22][C:21]([F:20])=[CH:31][CH:30]=3)[CH2:27]2)=[N:3][CH:4]=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 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 214287303-(4-Fluorophenoxy)azetidineHCID 866852613-((2-chloro-5-fluoropyrimidin-4-yl)amino)-N-methylbenzamide

生成物 1

HCID 533728583-((5-fluoro-2-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidin-4-yl)amino)-N-methylbenzamide収率 15%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 31374Dimethylacetamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-((2-chloro-5-fluoropyrimidin-4-yl)amino)-N-methylbenzamide (500 mg, 1.78 mmoL) and 3-(4-fluorophenoxy)azetidine (298 mg, 1.78 mmol) in DMA (6 mL, 3 mL/mmoL) was added cesium carbonate (580 mg, 2.67 mmol) and the reaction was degassed for 15 min. Pd2(dba)3 (80 mg, 0.089 mmol) and BINAP (55 mg, 0.089 mmol) and the reaction was allowed to heat at 100° C. in the microwave. The reaction was quenched with water and extracted with EtOAc (2×25 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure then purified by silica gel column chromatography to give 3-((5-fluoro-2-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidin-4-yl)amino)-N-methylbenzamide (97 mg, 15%) as solid. Observed mass (M+1): 412.1

後処理

  1. customthe reaction was degassed for 15 min
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc (2×25 mL)
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthen purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-6b1b78925275455db4d91b60006eb0d2
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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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート