Cesium carbonate → 2-Methyl-4-pyrrolidin-1-yl-quinoline-7-carboxylic acid (4-cyano-phenyl)-amide

HRID 1374754ノート

反応式

HRID 1374754 の反応式
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([C:17]([NH2:19])=[O:18])=[CH:7][CH:8]=2)[N:3]=1.I[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=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+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:25]([C:24]1[CH:27]=[CH:28][C:21]([NH:19][C:17]([C:6]2[CH:5]=[C:4]3[C:9]([C:10]([N:12]4[CH2:13][CH2:14][CH2:15][CH2:16]4)=[CH:11][C:2]([CH3:1])=[N:3]3)=[CH:8][CH:7]=2)=[O:18])=[CH:22][CH:23]=1)#[N:26]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 764674-IodobenzonitrileHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 694732582-Methyl-4-pyrrolidin-1-yl-quinoline-7-carboxylic acid amide

生成物 1

HCID 862184262-Methyl-4-pyrrolidin-1-yl-quinoline-7-carboxylic acid (4-cyano-phenyl)-amide収率 26%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

A suspension of 2-methyl-4-pyrrolidin-1-yl-quinoline-7-carboxylic acid amide (50 mg, 0.20 mmol), 4-iodobenzonitrile (45 mg, 0.20 mmol), xantphos (6.8 mg, 12 μmol), cesium carbonate (89 mg, 0.27 mmol), and palladium(II) acetate (1.8 mg, 8 μmol) in 1,4-dioxane (0.5 mL) was stirred under argon at 50° C. for 22 h, then the reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and dichloromethane. The organic layer was separated, washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, dichloromethane/methanol 19:1) afforded the title compound (18 mg, 26%). Light yellow solid, ISP-MS: m/e=357.3 ([M+H]+).

後処理

  1. customthe reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and dichloromethane
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

出典と根拠

ORDレコード
ord-98a1bcbf14fd45e0bf11c3eb7f7c0861
出典データセット
uspto-grants-2007_01
特許番号
US07166589B2

反応ノート

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