Potassium Phosphate, Tribasic → HCID 178435922, 화합물

HRID 1852840노트

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HRID 1852840 반응식
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

참가 물질

5

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 110316711-Phenylvinylboronic acid, pinacol esterHCID 178461197HCID 178461197, 화합물

생성물 1

HCID 178435922HCID 178435922, 화합물

시약·촉매·용매 1

HCID 178418807HCID 178418807, 화합물촉매

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온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-92be8c4679eb49209f88ad19a3dc0a4b
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962611B2

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