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

HRID 1640505노트

반응식

HRID 1640505 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-709bb9c77d504ad592fefaee9a63f50d
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114867B2

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