Potassium Phosphate, Tribasic → HCID 178435922、化合物

HRID 81235ノート

反応式

HRID 81235 の反応式
Br[C:2]1[N:19]([CH2:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]2)[C:5]2[C:6]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=3)=[N:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[N:3]=1.CC1(C)C(C)(C)OB([C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH2:37])O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[Cl:18][C:16]1[CH:17]=[C:12]([C:6]2[C:5]3[N:19]([CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]4)[C:2]([C:36]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH2:37])=[N:3][C:4]=3[CH:9]=[C:8]([C:10]#[N:11])[N:7]=2)[CH:13]=[N:14][CH:15]=1

参加物

5

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 110316711-Phenylvinylboronic acid, pinacol esterHCID 178461197HCID 178461197、化合物

生成物 1

HCID 178435922HCID 178435922、化合物

試薬・触媒・溶媒 1

HCID 178418807HCID 178418807、化合物触媒

反応条件

温度
50 °C

実験手順

A sealed tube was charged with 2-bromo-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (Preparative Example 3.1, 150 mg, 0.337 mmol), 4,4,5,5-tetramethyl-2-(1-phenylethenyl)-1,3,2-dioxaborolane (93 mg, 0.405 mmol), PdCl2(dppf)-dichloromethane adduct (27.5 mg, 0.034 mmol), and potassium phosphate (215 mg, 1.012 mmol). The tube was evacuated and backfilled with argon (3×). Fully degassed dioxane (1.53 mL) and water (0.153 mL) were added. The vial was sealed and heated at 50° C. overnight. The mixture was then cooled to room temperature and directly purified via silica gel chromatography (0-100% ethyl acetate/hexanes) to afford 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-(1-phenylethenyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile as a yellow solid. MS ESI calcd. for C28H26ClN5 [M+H]+ 468. found 468.

後処理

  1. customThe tube was evacuated
  2. additionFully degassed dioxane (1.53 mL) and water (0.153 mL) were added
  3. customThe vial was sealed
  4. temperatureThe mixture was then cooled to room temperature
  5. customdirectly purified via silica gel chromatography (0-100% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-a3a7ec8b04a94bc09bc86b1b6a7ecbef
出典データセット
uspto-grants-2014_09
特許番号
US08846657B2

反応ノート

読み込み中…