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Dichloromethane → 2-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-ylamine

HRID 570234
ノート
印刷プレビュー

反応式

HRID 570234 の反応式
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][CH2:7][CH2:8][O:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[C:14]([NH2:19])[CH:13]=[C:12](Cl)[N:11]=1)([CH3:4])([CH3:3])[CH3:2].[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+].C(Cl)Cl>O1CCOCC1.CCOC(C)=O.O>[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][CH2:7][CH2:8][O:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[C:14]([NH2:19])[CH:13]=[C:12]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[C:24]([F:35])([F:34])[F:23])[N:11]=1)([CH3:4])([CH3:3])[CH3:2]
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

8

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 866574152-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-6-chloro-3-nitro-pyridin-4-ylamine

生成物 1

HCID 674124792-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-ylamine

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

To a mixture of 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-6-chloro-3-nitro-pyridin-4-ylamine (1.20 g, 3.45 mmol, prepared as described in the previous step), 2-trifluoromethyl-phenyl-boronic acid (786 mg, 4.14 mmol), Cs2CO3 (2.81 g, 8.62 mmol) and Pd(dppf)2.DCM (282 mg, 0.345 mmol) in 1,4-dioxane (12 mL) was added water (5 mL). The resulting mixture was stirred at 110° C. under microwave irradiation for 2 h and then cooled to room temperature. The resulting mixture was treated with of EtOAc (50 mL), then washed with H2O and brine and was dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (5:95-40:60 EtOAc-hexanes) yielded 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-ylamine as a light brown solid. 1H-NMR (400 MHz, CDCl3) δ: 7.76 (d, J=7.8 Hz, 1H), 7.51-7.65 (m, 2H), 7.46 (d, J=7.3 Hz, 1H), 6.41 (s, 1H), 6.08 (br. s., 2H), 4.50 (t, J=5.3 Hz, 2H), 3.95 (t, J=5.3 Hz, 2H), 0.89 (s, 9H), 0.07 (s, 6H). Mass Spectrum (LCMS, ESI pos.) Calculated For C20H26F3N3O4Si: 458.1 (M+H), Measured: 458.0.

後処理

  1. customprepared
  2. temperaturecooled to room temperature
  3. washwashed with H2O and brine
  4. dry with materialwas dried (Na2SO4)
  5. customRemoval of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-73acb0b502a141ce9d2fa5a0b32bc1b5
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09023846B2

反応ノート

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