Triethylamine → HCID 71000688、化合物

HRID 1023454ノート

反応式

HRID 1023454 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]([NH2:12])=[O:11])[CH:4]=1)#[CH:2].[F:13][C:14]1[CH:19]=[CH:18][C:17](I)=[C:16]([CH3:21])[CH:15]=1.C(N(CC)CC)C.[NH4+].[Cl-]>CN(C=O)C.[Cl-].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd+2].[Cu]I.O>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]([NH2:12])=[O:11])[CH:4]=2)=[C:16]([CH3:21])[CH:15]=1

参加物

9

反応物 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27745254-Fluoro-1-iodo-2-methylbenzeneHCID 86673609HCID 86673609、化合物

生成物 1

HCID 71000688HCID 71000688、化合物収率 19.8%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 84124Bis(triphenylphosphine)palladium chloride触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

(4-Ethynyl-pyridin-2-yl)-urea (75 mg, 0.47 mmol), 4-fluoro-1-iodo-2-methyl-benzene (224 mg, 0.931 mmol), triethylamine (5.0 mL), palladium bis(triphenylphosphine)dichloride (16 mg, 0.023 mmol) and Copper (I) iodide (8.8 mg, 0.047 mmol) are mixed in DMF (1.8 mL). The reaction mixture is stirred for 16 hrs at room temperature before saturated NH4Cl solution (5 mL) is added along with water (25 mL). The mixture is extracted with EtOAc (3×20 mL) and the organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 5%) affords 25 mg of the desired product.

後処理

  1. extractionThe mixture is extracted with EtOAc (3×20 mL)
  2. concentrationconcentrated
  3. customto give the crude product
  4. customPurification by silica flash column chromatography

出典と根拠

ORDレコード
ord-35fd92374f414824a16e4b2b340967da
出典データセット
uspto-grants-2014_05
特許番号
US08722709B2

反応ノート

読み込み中…