3-Fluoroazetidine → HCID 90333604, 화합물

HRID 595735

반응식

HRID 595735 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH:7]([CH2:12][CH:13]=O)[N:6]3[C:15]4[CH:16]=[CH:17][CH:18]=[C:19]([F:22])[C:20]=4[CH:21]=[C:5]3[C:4]=2[N:3]=1.[F:23][CH:24]1[CH2:27][NH:26][CH2:25]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH:7]([CH2:12][CH2:13][N:26]3[CH2:27][CH:24]([F:23])[CH2:25]3)[N:6]3[C:15]4[CH:16]=[CH:17][CH:18]=[C:19]([F:22])[C:20]=4[CH:21]=[C:5]3[C:4]=2[N:3]=1

참가 물질

5

반응물 3

HCID 36035423-FluoroazetidineHCID 5049666Sodium triacetoxyborohydrideHCID 90333623HCID 90333623, 화합물

생성물 1

HCID 90333604HCID 90333604, 화합물수율 43.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-(2-chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-6-yl)acetaldehyde (200 mg, 0.617 mmol) and 3-fluoroazetidine (95 mg, 1.23 mmol) in DCM (4 mL) was stirred at room temperature for 30 minutes under N2. Then Na(OAc)3BH (50 mg) was added to the mixture, and the mixture was stirred at room temperature for 1 hour. After dilution with water (30 mL) and extraction with EA (20 mL×3), the organic layer was washed with brine (30 mL*3), dried over Na2SO4 and concentrated. The residue was purified by column chromatography (PE:EA=1:1) to afford the desired product of 2-chloro-11-fluoro-6-(2-(3-fluoroazetidin-1-yl)ethyl)-5,6-dihydroindolo[1,2-h][1,7]naphthyridine (100 mg, yield: 43%). 1H-NMR (CDCl3, 400 MHz) δ 7.44 (d, J=8.0 Hz, 1H), 7.3 (s, 1H), 7.16 (d, J=8.0 Hz, 1H), 7.10 (t, J=4.8 Hz, J=2.7 Hz, 2H), 6.69˜6.74 (m, 1H), 5.11˜5.14 (m, 0.5H), 4.97˜4.50 (m, 0.5H), 4.87 (t, J=4.8 Hz, 1H), 3.57 (d, J=6.8 Hz, 1H), 3.33˜3.39 (m, 1H), 2.95˜3.06 (m, 2H), 2.2˜72.38 (m, 1H). MS (M+H)+: 374/376.

후처리

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionAfter dilution with water (30 mL) and extraction with EA (20 mL×3)
  3. washthe organic layer was washed with brine (30 mL*3)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (PE:EA=1:1)

출처 및 근거

ORD 기록
ord-1fed303d4b3f4705afea55f1a59cb280
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

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