Potassium Carbonate → HCID 86625879, 화합물

HRID 2421991노트

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HRID 2421991 반응식
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH:13]1[CH2:16][CH:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:14]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:8][C:7]1[C:2]([N:13]2[CH2:16][CH:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:14]2)=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 15194053-Aminoazetidine, 3-BOC protected

생성물 1

HCID 86625879HCID 86625879, 화합물수율 34.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

2,3-Dichloro-5-(trifluoromethyl)pyridine (1.50 g, 6.94 mmol), tert-butyl azetidin-3-ylcarbamate (1.67 g, 9.72 mmol) and K2CO3 (2.88 g, 20.83 mmol) were dissolved in dry DMF (13 mL) under nitrogen atmosphere. The reaction mixture was heated in a microwave reactor at 150° C. for 15 mins. The reaction mixture was filtered and diluted with EtOAc, washed with water, dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography (ISOLUTE SI (20 g), eluated with DCM, DCM/MeOH (99:1)) affording the title compound (0.85 g, 34.8%). 1H NMR (500 MHz, CDCl3): δ 1.48 (s, 9H), 4.10-4.14 (m, 2H), 4.57 (bs, 1H), 4.65 (t, 2H), 5.00 (bs, 1H), 7.61 (s, 1H), 8.28 (s, 1H); 13C NMR (125 MHz, CDCl3): δ 28.56, 41.67, 60.34, 80.45, 115.51, 117.44 (q, JC-F=33.2 Hz), 123.83 (m, JC-F=271.4 Hz), 135.06, 143.75, 155.18, 157.35; Mass Spectrum: M−H+ 350.

후처리

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with EtOAc
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography (ISOLUTE SI (20 g), eluated with DCM, DCM/MeOH (99:1))

출처 및 근거

ORD 기록
ord-193495014f394378854c44ac9f3700d5
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960380B2

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