Water → [4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-6-phenyl-pyridin-2-yl]-methyl-amine

HRID 383321노트

반응식

HRID 383321 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[CH:5]=[C:4]([C:10]2[N:14]3[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]3=[N:12][CH:11]=2)[CH:3]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:19][C:17]1[CH:16]=[CH:15][N:14]2[C:10]([C:4]3[CH:3]=[C:2]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:7]=[C:6]([NH:8][CH3:9])[CH:5]=3)=[CH:11][N:12]=[C:13]2[CH:18]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86644347[6-Chloro-4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-pyridin-2-yl]-methyl-amine

생성물 1

HCID 68487387[4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-6-phenyl-pyridin-2-yl]-methyl-amine

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

[6-Chloro-4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-pyridin-2-yl]-methyl-amine (1 eq, 0.19 mmol, 56 mg) and phenylboronic acid (1.1 eq, 0.21 mmol, 25.6 mg) are dissolved in DME (2 ml) and water (0.5 ml) and Na2CO3 (1.5 eq, 0.29 mmol, 35.5 mg) is added. PdCl2(PPh3)2 (0.1 eq, 0.019 mmol, 13.4 mg) is added and the reaction mixture is heated using microwave radiation at 120° C. for 10 min. At the completion of this time the solvent is removed in vacuo and the reaction mixture is purified by flash column chromatography eluting with 9:1 DCM/MeOH to yield [4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-6-phenyl-pyridin-2-yl]-methyl-amine as a brown solid; [M+H]+=335

후처리

  1. temperaturethe reaction mixture is heated
  2. customat 120° C.
  3. customfor 10 min
  4. customAt the completion of this time the solvent is removed in vacuo
  5. customthe reaction mixture is purified by flash column chromatography
  6. washeluting with 9:1 DCM/MeOH

출처 및 근거

ORD 기록
ord-296c6d70a8dd41749379eaa5f8a9f56b
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367662B2

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