Cesium carbonate → HCID 86648952, 화합물

HRID 449887노트

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HRID 449887 반응식
Br[C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:18])[C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])[CH:5]=[CH:4][N:3]=1.[Cl:19][C:20]1[N:25]=[C:24]([NH2:26])[CH:23]=[C:22]([CH:27]([CH3:29])[CH3:28])[N:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.COCCOC>[Cl:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([Cl:16])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:26][C:24]2[CH:23]=[C:22]([CH:27]([CH3:28])[CH3:29])[N:21]=[C:20]([Cl:19])[N:25]=2)[CH:7]=1)=[O:18]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 735550432-Chloro-6-isopropylpyriMidin-4-aMineHCID 75464886N-(2-Bromopyridin-4-yl)-2,6-dichlorobenzamide

생성물 1

HCID 86648952HCID 86648952, 화합물수율 117.7%

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a microwave tube was added N-(2-bromopyridin-4-yl)-2,6-dichlorobenzamide (0.25 g, 0.72 mmol), 2-chloro-6-isopropylpyrimidin-4-amine (0.16 g, 0.94 mmol), Pd2(dba)3 (0.020 g, 0.022 mmol), XantPhos (0.008 g, 0.014 mmol), Cs2CO3 (0.47 g, 1.4 mmol) dioxane (20 mL) and DME (5 mL). The mixture was degassed with N2 for 10 min. The resulting mixture was irradiated in a microwave reactor at 130° C. for 2 hours and then cooled to room temperature. The mixture was filtered through Celite and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc/Petrolum ether=20/80 to 30/70) to give 2,6-dichloro-N-(2-(2-chloro-6-isopropylpyrimidin-4-ylamino)pyridin-4-yl)benzamide (370 mg, yield: 90%). LCMS (ESI) m/z: 436.0 [M+H+].

후처리

  1. customThe mixture was degassed with N2 for 10 min
  2. customThe resulting mixture was irradiated in a microwave reactor at 130° C. for 2 hours
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (EtOAc/Petrolum ether=20/80 to 30/70)

출처 및 근거

ORD 기록
ord-1dc9c1dd59374bdf9455eee1c09050c4
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486950B2

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