Dichloromethane → HCID 117732307、化合物

HRID 1772737

反応式

HRID 1772737 の反応式
Br[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([Cl:9])=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:18]2[CH:19]=[CH:20][C:21]([N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)=[N:22][CH:23]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+].C(Cl)Cl>O1CCOCC1.CCOC(C)=O.O>[NH2:8][C:6]1[N:7]=[C:2]([C:18]2[CH:19]=[CH:20][C:21]([N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)=[N:22][CH:23]=2)[CH:3]=[N:4][C:5]=1[Cl:9]

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 16217947Tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylateHCID 569657236-Bromo-3-chloropyrazin-2-amine

生成物 1

HCID 117732307HCID 117732307、化合物

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
90 °C

実験手順

To a mixture of 6-bromo-3-chloropyrazin-2-amine (2.00 g, 9.60 mmol), tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate (3.74 g, 9.60 mmol), Cs2CO3 (7.82 g, 24.0 mmol), and Pd(dppf)2.CH2Cl2 (786 mg, 0.959 mmol) in 1,4-dioxane (40 mL) was added water (20 mL). The resulting mixture was stirred at 90° C. for 16 h and then cooled to rt. The reaction mixture was diluted with EtOAc (300 mL), then washed with water (2×50 mL) and brine (50 mL). Removal of the solvent under reduced pressure followed by purification by flash column chromatography on silica gel (0-3% MeOH/DCM) gave compound 87a as a yellow solid. 1H-NMR (CDCl3; 400 MHz) δ 8.75 (d, J=2.2 Hz, 1H), 8.01-8.09 (m, 2H), 6.70 (d, J=9.0 Hz, 1H), 5.02 (br. s., 2H), 3.60-3.69 (m, 4H), 3.57 (br. s., 4H), 1.49 (s, 9H). Mass spectrum (LCMS, ESI pos.): Calcd. for C18H23ClN6O2, 391.1 (M+H). found 391.1.

後処理

  1. temperaturecooled to rt
  2. washwashed with water (2×50 mL) and brine (50 mL)
  3. customRemoval of the solvent under reduced pressure
  4. customfollowed by purification by flash column chromatography on silica gel (0-3% MeOH/DCM)

出典と根拠

ORDレコード
ord-d39651180ea5457b9ebc9fcadf55ff33
出典データセット
uspto-grants-2016_02
特許番号
US09249163B2

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