Ethyl Acetate → [3-(6-Methoxy-[1,5]naphthyridin-4-yl)-prop-2-ynyl]-carbamic acid tert-butyl ester

HRID 1640505ノート

反応式

HRID 1640505 の反応式
[C:1]([NH:8][CH2:9][C:10]#[CH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:13]1[CH:14]=[CH:15][N:16]=[C:17]2[C:22]=1[N:21]=[C:20]([O:23][CH3:24])[CH:19]=[CH:18]2.CC(=O)OCC>CN(C=O)C.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.[Cu]I>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][C:10]#[C:11][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[N:21]=2)[N:16]=[CH:15][CH:14]=1)([CH3:5])([CH3:6])[CH3:7]

参加物

7

反応物 3

HCID 8857Ethyl AcetateHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 534216178-Bromo-2-methoxy-1,5-naphthyridine

生成物 1

HCID 66737778[3-(6-Methoxy-[1,5]naphthyridin-4-yl)-prop-2-ynyl]-carbamic acid tert-butyl ester収率 44.3%

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 6228Dimethylformamide溶媒

実験手順

To a solution of N-Boc propargyl amine (3.25 g, 20.9 mmol) and 8-bromo-2-methoxy-[1,5]naphthyridine (5.00 g, 20.9 mmol; prepared as in WO 2006/032466) and TEA (17.5 mL, 6 eq.) in DMF (120 mL) were added Pd(PPh3)2Cl2 (755 mg, 1.08 mmol) and CuI (432 mg, 2.27 mmol). The mixture was degassed with a stream of N2 for 15 min and then stirred at rt for 5 h. The mixture was partitioned between water and EA, the org. layer was washed several times with water and a sat. NH4Cl solution, dried over MgSO4 and concentrated. Chromatography on SiO2 (Hex/EA 1:1, EA) gave the coupling product as a beige solid (2.90 g, 44% yield).

後処理

  1. customThe mixture was degassed with a stream of N2 for 15 min
  2. customThe mixture was partitioned between water and EA
  3. washlayer was washed several times with water
  4. dry with materiala sat. NH4Cl solution, dried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-709bb9c77d504ad592fefaee9a63f50d
出典データセット
uspto-grants-2012_02
特許番号
US08114867B2

反応ノート

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