Cesium carbonate → HCID 86648952、化合物

HRID 449887ノート

反応式

HRID 449887 の反応式
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]

参加物

7

反応物 3

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

生成物 1

HCID 86648952HCID 86648952、化合物収率 117.7%

試薬・触媒・溶媒 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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+].

後処理

  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)

出典と根拠

ORDレコード
ord-1dc9c1dd59374bdf9455eee1c09050c4
出典データセット
uspto-grants-2013_07
特許番号
US08486950B2

反応ノート

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