Triethylamine → 2-(1-BOC-2-(S)-pyrrolidinyl)furo[3,2-b]pyridine

HRID 611554

반응식

HRID 611554 반응식
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]#[CH:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.I[C:23]1[C:28]([OH:29])=[CH:27][CH:26]=[CH:25][N:24]=1>CN(C=O)C.C1(C)C=CC=CC=1.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:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:29][C:28]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 971792-Iodopyridin-3-olHCID 11030701(S)-N-Boc-2-ethynylpyrrolidine

생성물 1

HCID 153897342-(1-BOC-2-(S)-pyrrolidinyl)furo[3,2-b]pyridine

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

A 2.34 g (12 mmol) sample of the compound from step 1c above was dissolved in 15 mL of DMF, and (Ph3P)2PdCl2 (0.6 mmol), CuI (0.74 mmol) and triethylamine (14.25 mmol) were added. The mixture was stirred at room temperature for 1 hour, then 3.14 g (14.4 mmol) of 2-iodo-3-hydroxypyridine (Lancaster Chem. Co.) was added. The reaction mixture was stirred at 60° C. for 16 hours. The solution was cooled, diluted with toluene, and the volatiles were removed under reduced pressure. The residue was dissolved in 1 N HCl, and this solution was extracted with ether. The acidic aqueous layer was adjusted to pH 10 with K2CO3, and this solution was extracted with CH2Cl2. The CH2Cl2 extract was washed with 20% Na,OH, dried over MgSO4, and evaporated. The residue was chromatographed on silica gel, eluting with 100:0 to 95:5 CHCl3 :MeOH to give 980 mg of title compound: 1H NMR (CDCl3, 300 MHz) δ 1.32 (s, 9H), 1.90-2.20 (m, 4H), 2.95-3.15 (m, 2H), 5.05 (m, 1H), 6.68 (s, 1H), 7.15 (br s, 1H), 7.67 (d, 1H, J=8 Hz), 8.48 (d, 1H, J=3 Hz); MS m/z: 289 (M+H)+.

후처리

  1. stirringThe reaction mixture was stirred at 60° C. for 16 hours
  2. temperatureThe solution was cooled
  3. customthe volatiles were removed under reduced pressure
  4. dissolutionThe residue was dissolved in 1 N HCl
  5. extractionthis solution was extracted with ether
  6. extractionthis solution was extracted with CH2Cl2
  7. extractionThe CH2Cl2 extract
  8. washwas washed with 20% Na,OH
  9. dry with materialdried over MgSO4
  10. customevaporated
  11. customThe residue was chromatographed on silica gel
  12. washeluting with 100:0 to 95:5 CHCl3

출처 및 근거

ORD 기록
ord-252b0b72149540b6b29b0f947b513751
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06001849

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