Cesium carbonate → Tert-butyl 7-(4-(5-chloropyridin-2-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylate

HRID 1626389ノート

反応式

HRID 1626389 の反応式
[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:15][O:16]3)=[CH:11][C:10]=2[C:26]#[N:27])=[CH:6][CH:5]=1)(=[O:3])[NH2:2].Cl[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][N:32]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([NH:2][C:1]([C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]3[CH:18]=[C:17]4[C:12]([CH:13]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:14][CH2:15][O:16]4)=[CH:11][C:10]=3[C:26]#[N:27])=[CH:28][CH:29]=2)=[O:3])=[N:32][CH:33]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 276852,5-DichloropyridineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86664391tert-Butyl 7-(4-carbamoylphenoxy)-6-cyanochroman-4-carboxylate

生成物 1

HCID 67288859Tert-butyl 7-(4-(5-chloropyridin-2-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylate収率 13%

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
80 °C

実験手順

tert-Butyl 7-(4-carbamoylphenoxy)-6-cyanochroman-4-carboxylate (30 mg, 0.076 mmol), 2,5-dichloropyridine (12 mg, 0.084 mmol), XPHOS (7.3 mg, 0.015 mmol), palladium (II) acetate (1.7 mg, 0.0076 mmol) and cesium carbonate (62 mg, 0.19 mmol) were diluted with dioxane (600 μL) in a 1 mL vial. The reaction was purged with argon for 3 minutes, capped and heated at 80° C. for 12 hours. The reaction was cooled and loaded directly onto a biotage 25 column and eluted with 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes to yield tert-butyl 7-(4-(5-chloropyridin-2-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylate (5 mg, 0.0099 mmol, 13% yield).

後処理

  1. customThe reaction was purged with argon for 3 minutes
  2. customcapped
  3. temperatureThe reaction was cooled
  4. washeluted with 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-73182cd5232a453a982e1900512da314
出典データセット
uspto-grants-2014_07
特許番号
US08785445B2

反応ノート

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