Cesium carbonate → HCID 49839566、化合物

HRID 449881

反応式

HRID 449881 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.[NH2:19][C:20]1[O:21][CH:22]=[CH:23][N:24]=1.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.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].O1CCOCC1>[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:19][C:20]2[O:21][CH:22]=[CH:23][N:24]=2)[CH:7]=1)=[O:18]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 5585212-AminooxazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 75464886N-(2-Bromopyridin-4-yl)-2,6-dichlorobenzamide

生成物 1

HCID 49839566HCID 49839566、化合物収率 9%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

To a microwave tube was added N-(2-bromopyridin-4-yl)-2,6-dichlorobenzamide (0.30 g, 0.87 mmol), 2-aminooxazole (0.11 g, 1.0 mmol), Pd2(dba)3 (0.078 g, 0.087 mmol), XantPhos (0.096 g, 0.17 mmol), Cs2CO3 (0.57 g, 1.7 mmol) and dioxane (5 mL). The mixture was degassed with N2 for 10 min. The resulting mixture was irradiated in a microwave reactor at 140° C. for 3 hours and then cooled to room temperature. The mixture was filtered through Celite and concentrated under reduced pressure. The residue was dissolved in DMF and purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to give the desired product as a yellow solid (26 mg, yield: 9%). 1H NMR (500 MHz, DMSO-d6): δ 11.2 (s, 1H), 8.28 (s, 1H), 8.17 (d, J=5.5 Hz, 1H), 7.71 (s, 1H), 7.59 (d, J=7.5 Hz, 2H), 7.52 (t, J=3.5 Hz, 1H), 7.41 (m, 1H), 7.03 (s, 1H). LC-MS (ESI) m/z: 349.0 [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 140° C. for 3 hours
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in DMF
  6. custompurified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min)

出典と根拠

ORDレコード
ord-4deb55779a0a435eab3663dfe7a419cd
出典データセット
uspto-grants-2013_07
特許番号
US08486950B2

関連ノート

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