Cesium carbonate → HCID 59618183、化合物

HRID 449889ノート

反応式

HRID 449889 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.[CH3:19][N:20]1[CH:24]=[CH:23][C:22]([NH2:25])=[N:21]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:25][C:22]2[CH:23]=[CH:24][N:20]([CH3:19])[N:21]=2)[CH:7]=1)=[O:18]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 1372541-Methyl-3-aminopyrazoleHCID 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 59618183HCID 59618183、化合物収率 24%

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 were added N-(2-bromopyridin-4-yl)-2,6-dichlorobenzamide (0.12 g, 0.36 mmol), 1-methyl-1H-pyrazol-3-amine (0.045 g, 0.46 mmol), Pd2(dba)3 (0.031 g, 0.033 mmol), XantPhos (0.031 g, 0.052 mmol), Cs2CO3 (0.31 g, 0.94 mmol) and dioxane (3 mL). The mixture was degassed with N2 for 10 min. The resulting mixture was irradiated in a microwave reactor at 140° C. for 1 hour and then cooled to room temperature. The mixture was filtered through Celite and concentrated under reduced pressure. The residue was 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 (30 mg, yield: 24%). 1H NMR (500 MHz, DMSO-d6): δ 10.92 (s, 1H). 9.16 (s, 1H), 8.01 (m, 1H), 7.60-7.50 (m, 5H), 7.04 (d, J=4.0 Hz, 1H), 6.27 (d, J=1.5 Hz, 1H), 3.72 (s, 3H). LCMS (ESI) m/z: 362.0 [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 1 hour
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated under reduced pressure
  5. 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-5595a9cc5f6545fbb3fc58af4c77c383
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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