Triethylamine → HCID 57962721、化合物

HRID 541858ノート

反応式

HRID 541858 の反応式
I[C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:23]([C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28])#[CH:24]>O1CCCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:28][C:27]1[CH:26]=[C:25]([C:23]#[C:24][C:2]2[N:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:4][CH:3]=2)[CH:31]=[CH:30][CH:29]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 104682Benzenamine, 3-ethynyl-HCID 24229165tert-Butyl (6-iodopyridin-2-yl)carbamate

生成物 1

HCID 57962721HCID 57962721、化合物収率 89%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

tert-Butyl (6-iodopyridin-2-yl)carbamate (1.50 g, 4.68 mmol), copper(I) iodide (68.0 mg, 0.36 mmol) and bis(triphenylphosphine)palladium(II) chloride (100 mg, 0.2 mmol) were stirred in tetrahydrofuran (14 mL) with triethylamine (0.70 mL, 5.0 mmol) under N2 at rt. 3-Ethynylaniline (0.47 mL, 4.5 mmol) was added and the mixture was heated at 60° C. overnight. The mixture was filtered, washed with EtOAc and concentrated under vacuum to give the desired product as a brown solid (1.23 g, 89%). LCMS for C14H12N3O2 ([M-(tBu)+H]+H)+: m/z=254.1.

後処理

  1. filtrationThe mixture was filtered
  2. washwashed with EtOAc
  3. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-c7665e420b864b4c8351c49d852881d7
出典データセット
uspto-grants-2014_10
特許番号
US08871753B2

反応ノート

読み込み中…