Triethylamine → 3-(1-Boc-2-(r)-azetidinylmethoxy)-6-chloro-5-(trimethylsilylethynyl)pyridine

HRID 2305198

반응식

HRID 2305198 반응식
[C:1]([N:8]1[CH2:11][CH2:10][C@@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][C:17]([Cl:21])=[C:18](Br)[CH:19]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(CC)CC.[CH3:29][Si:30]([C:33]#[CH:34])([CH3:32])[CH3:31]>C1(C)C=CC=CC=1.[I+].[Cu+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([N:8]1[CH2:11][CH2:10][C@@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][C:17]([Cl:21])=[C:18]([C:34]#[C:33][Si:30]([CH3:32])([CH3:31])[CH3:29])[CH:19]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 229618073-(1-Boc-2-(r)-azetidinylmethoxy)-5-bromo-6-chloropyridine

생성물 1

HCID 229618103-(1-Boc-2-(r)-azetidinylmethoxy)-6-chloro-5-(trimethylsilylethynyl)pyridine수율 62.2%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 178505377HCID 178505377, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To a solution of 3-(1-BOC-2-(R)-azetidinylmethoxy)-6-chloro-5-bromopyridine (660 mg, 1.75 mmol) in toluene (20 mL) was added NEt3 (0.7 mL), copper (I) iodine (33 mg), tetrakis(triphenylphosphine)palladium (0) (201 mg) and (trimethylsilyl)acetylene (0.30 mL, 2.10 mmol). The reaction mixture was stirred and heated at 100° C. for 16 h. Solvent was evaporated and the residue was chromatographed (silica gel; hexane/EtoAc, 5:1 to 2:1) to afford an oil (430 mg, 62%): 1H NMR (CDCl3, 300 MHz) δ 1.42 (s, 9H), 2.20-2.40 (m, 2H), 3.80-3.92 (m, 2H), 4.10 (m, 1H), 4.30 (m,1H), 4.50 (m, 1H), 7.37 (d, 1H, J=3.0 Hz), 8.05 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 395 (M+H)+.

후처리

  1. customSolvent was evaporated
  2. customthe residue was chromatographed (silica gel; hexane/EtoAc, 5:1 to 2:1)

출처 및 근거

ORD 기록
ord-0f8336b224414bbc84aeb43735409178
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06437138B1

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