Triethylamine → 2-(2-(Tetrahydropyran-4-yl)ethyl)benzoxazole

HRID 74263노트

반응식

HRID 74263 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=C[C:3]=1[N+]([O-])=O.[O:20]1CCC(CCN)[CH2:22][CH2:21]1.C(N(CC)CC)C.[H][H]>[C].[Pd].O.C(#N)C>[O:20]1[CH2:3][CH2:2][CH:7]([CH2:6][CH2:5][C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:22][CH2:21]1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 27731982-(Oxan-4-yl)ethan-1-amineHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 674986762-(2-(Tetrahydropyran-4-yl)ethyl)benzoxazole수율 62.8%

시약·촉매·용매 3

HCID 178418390HCID 178418390, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

2-(4-Fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (800 mg, 3.1 mmol) was added to an acetonitrile (5 mL) solution containing 2-(tetrahydropyran-4-yl)ethylamine (520 mg, 3.9 mmol) and triethylamine (500 mg, 3.9 mmol), and this was heated to reflux for 3 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a tetrahydrofuran solution (20 mL) of the crystals obtained was added 10% palladium-carbon (100 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred overnight at room temperature. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (450 mg, 43% yield) as a syrup.

후처리

  1. temperaturethis was heated
  2. temperatureto reflux for 3 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a tetrahydrofuran solution (20 mL) of the crystals obtained
  7. filtrationthis was filtered through Celite
  8. concentrationthe filtrate was concentrated
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-03e46c74cfcc46ce80ee728acd94820c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

반응 노트

불러오는 중…