Dichloromethane → 7-(6-Chloropyridin-3-yl)-N-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 335280

반응식

HRID 335280 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([C:20](=[O:31])[NH:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=4)[CH:17]=[CH:16][C:15]=3[F:32])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.[Cl:33][C:34]1[N:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>COCCOC.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].O>[Cl:33][C:34]1[N:39]=[CH:38][C:37]([C:2]2[CH:7]=[CH:6][N:5]3[C:8]([C:11]([NH:13][C:14]4[CH:19]=[C:18]([C:20](=[O:31])[NH:21][CH2:22][C:23]5[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=5)[CH:17]=[CH:16][C:15]=4[F:32])=[O:12])=[CH:9][N:10]=[C:4]3[CH:3]=2)=[CH:36][CH:35]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 38450342-Chloropyridine-5-boronic acidHCID 712831817-bromo-N-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide2회

생성물 1

HCID 866956757-(6-Chloropyridin-3-yl)-N-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture comprising 7-bromo-N-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide (Intermediate 3A) 100 mg, 0.199 mmol), 6-chloropyridin-3-ylboronic acid (31.3 mg, 0.199 mmol) and cesium carbonate (259 mg, 0.795 mmol) in DME (631 μL)/water (31.5 μL) was purged with nitrogen and treated with PdCl2(dppf).CH2Cl2 adduct (8.11 mg, 9.93 μmol) The resulting mixture was heated using microwave radiation at 100° C. for 15 mins. The water was removed by pipette and the reaction mixture was diluted with MeOH. Purification of the mixture by chromatography on silica eluting with 0-20% 2M NH3 in MeOH/DCM afforded the title compound;

후처리

  1. customat 100° C.
  2. customfor 15 mins
  3. customThe water was removed by pipette
  4. additionthe reaction mixture was diluted with MeOH
  5. customPurification of the mixture by chromatography on silica eluting with 0-20% 2M NH3 in MeOH/DCM

출처 및 근거

ORD 기록
ord-ae27f1868b2a41f6aa992461d0867954
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883819B2

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