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Potassium Phosphate, Tribasic → (1R,5S,6R)-5-(difluoromethyl)-5-(2-fluoro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)phenyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine

HRID 1526657
ノート
印刷プレビュー

反応式

HRID 1526657 の反応式
P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[CH:11]=[CH:12][C:13]([F:27])=[C:14]([C@:16]2([CH:24]([F:26])[F:25])[C@@H:22]3[C@@H:20]([CH2:21]3)[O:19][C:18]([NH2:23])=[N:17]2)[CH:15]=1.[C:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[N:35][CH:36]=1)#[C:29][CH3:30]>O1CCOCC1.O.O.C(C1C(C(C)(C)C)=C([Pd]Cl)C=CC=1NC)(C)(C)C>[F:25][CH:24]([F:26])[C@@:16]1([C:14]2[CH:15]=[C:10]([C:33]3[CH:34]=[N:35][CH:36]=[C:31]([C:28]#[C:29][CH3:30])[CH:32]=3)[CH:11]=[CH:12][C:13]=2[F:27])[C@@H:22]2[C@@H:20]([CH2:21]2)[O:19][C:18]([NH2:23])=[N:17]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 3

HCID 62657Potassium Phosphate, TribasicHCID 574164825-(1-Propynyl)pyridine-3-boronic Acid (contains varying amounts of Anhydride)HCID 90401254(1R,5S,6R)-5-(5-bromo-2-fluorophenyl)-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine

生成物 1

HCID 90413015(1R,5S,6R)-5-(difluoromethyl)-5-(2-fluoro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)phenyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine収率 74%

試薬・触媒・溶媒

3
HCID 178482226HCID 178482226、化合物触媒HCID 962Water溶媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
110 °C

実験手順

A microwave vial was charged with mixture of potassium phosphate (0.19 g, 0.90 mmol), (1R,5S,6R)-5-(5-bromo-2-fluorophenyl)-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine (16f-B, 0.10 g, 0.30 mmol), (5-(prop-1-yn-1-yl)pyridin-3-yl)boronic acid (0.12 g, 0.75 mmol) and 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium(II) chloride (10.56 mg, 0.015 mmol) in dioxane/water (2.0/0.5 mL). The reaction mixture was heated to 110° C. for 30 min in the microwave. The reaction mixture was then diluted with water and extracted with DCM three times. The combined organic extracts were washed with brine and dried over sodium sulfate. The filtrate was concentrated in vacuo and the crude material was purified by silica gel chromatography (0-100% EtOAc-DCM) to obtain the title compound as a white solid (82.3 mg, 74% yield). MS m/z=372 [M+H]+. Calculated for C20H16F3N3O: 371.4.

後処理

  1. extractionextracted with DCM three times
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe crude material was purified by silica gel chromatography (0-100% EtOAc-DCM)

出典と根拠

ORDレコード
ord-43ea1044f7ad414ca637e1665872f32e
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085576B2

反応ノート

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