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

HRID 611565노트

반응식

HRID 611565 반응식
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1I.C(N(CC)CC)C.[C:16]([N:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[C:28]#[CH:29])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CN(C=O)C.CCOCC.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:16]([N:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[C:28]1[O:1][C:2]2=[CH:3][N:4]=[CH:5][CH:6]=[C:7]2[CH:29]=1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 11030701(S)-N-Boc-2-ethynylpyrrolidineHCID 225035814-Iodopyridin-3-ol

생성물 1

HCID 183962352-(1-BOC-2-(S)-pyrrolidinyl)furo[2,3-c]pyridine

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매2회

실험 절차

A 829 mg (3.7 mmol) sample of 3-hydroxy-4-iodopyridine, from step 9b above, 130 mg (0.18 mmol) of (Ph3P)2PdCl2, 170 mg (0.74 mmol) of CuI, and 0.6 mL of triethylamine were combined in 10 mL of DMF at ambient temperature and stirred for 3 hours. To this mixture was added a solution of 1-BOC-2-(S)-ethynylpyrrolidine (1.5 g, 7.7 mmol, from Example 1c above) in 5 mL of DMF, and the reaction mixture was stirred at 60° C. for 16 hours. The reaction mixture was cooled to room temperature and diluted with ether. The ether layer was filtered, washed with 10% NaOH then 50% brine, dried over MgSO4, and concentrated. The residue was purified by chromatography on silica gel, eluting with 100:0 to 50:50 hexane:EtOAc to give the title compound.

후처리

  1. stirringthe reaction mixture was stirred at 60° C. for 16 hours
  2. filtrationThe ether layer was filtered
  3. washwashed with 10% NaOH
  4. dry with material50% brine, dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with 100:0 to 50:50 hexane

출처 및 근거

ORD 기록
ord-be2a1a9a5a634900aec9171d5fda877c
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06001849

반응 노트

불러오는 중…