Sodium Carbonate → 1-[6-[3-(4-Morpholinyl)-5-nitrophenyl]-2-pyridinyl]cyclobutanol

HRID 2207352노트

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HRID 2207352 반응식
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[N:13]=[C:12]([C:14]2([OH:18])[CH2:17][CH2:16][CH2:15]2)[CH:11]=[CH:10][CH:9]=1.[N+:19]([C:22]1[CH:23]=[C:24]([N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH:25]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:27]=1)([O-:21])=[O:20]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[N:37]1([C:24]2[CH:25]=[C:26]([C:8]3[N:13]=[C:12]([C:14]4([OH:18])[CH2:17][CH2:16][CH2:15]4)[CH:11]=[CH:10][CH:9]=3)[CH:27]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 589324181-(6-Bromopyridin-2-yl)cyclobutanolHCID 672568704-(3-Nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine

생성물 1

HCID 1180930551-[6-[3-(4-Morpholinyl)-5-nitrophenyl]-2-pyridinyl]cyclobutanol

시약·촉매·용매 1

HCID 178418807HCID 178418807, 화합물촉매

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온도
100 °C

실험 절차

Pd(dppf)Cl2-dichloromethane adduct (40.8 mg, 0.05 mmol) and sodium carbonate (2 N, 1.5 mL, 3.0 mmol) were added to 1-(6-bromopyridin-2-yl)cyclobutanol (228 mg, 1.0 mmol) and 4-[3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine (0.2 N in DMF, 5.0 mL, 1.0 mmol) and the reaction mixture was purged and flushed with N2(g) (3×). The reaction mixture was heated to 100° C. for 4 hours, then cooled to room temperature, diluted with water, extracted with diethyl ether, washed with brine, dried over sodium sulfate, filtered an concentrated under reduced pressure. The crude product was purified by silica gel chromatography (ethyl acetate:hexanes) to afford 1-{6-[3-(morpholin-4-yl)-5-nitrophenyl]pyridin-2-yl}cyclobutanol. 1H NMR (500 MHz, CDCl3) δ 8.30-8.23 (m, 1H), 7.98-7.95 (m, 1H), 7.93, (t, J=7.2 Hz 1H), 7.79 (t, J=2.2, 1H), 7.74 (d, J=7.8, 1H), 7.66 (d, J=7.8, 1H), 5.36 (s, 1H), 4.03-3.84 (m, 4H), 3.46-3.29 (m, 4H), 2.82-2.47 (m, 4H), 2.27-2.09 (m, 1H), 2.05-1.91 (m, 1H).

후처리

  1. customthe reaction mixture was purged
  2. customflushed with N2(g) (3×)
  3. temperaturecooled to room temperature
  4. additiondiluted with water
  5. extractionextracted with diethyl ether
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationan concentrated under reduced pressure
  10. customThe crude product was purified by silica gel chromatography (ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-8764354602794e96b2b97a97ed28a52b
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376418B2

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