Triphenylphosphine → Methyl 6-(tert-butoxycarbonyl(4,4,4-trifluoro-1-(4'-(trifluoromethyl)biphenyl-4-yl)butyl)amino)nicotinate

HRID 1427509

반응식

HRID 1427509 반응식
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[F:15][C:16]([F:38])([F:37])[CH2:17][CH2:18][CH:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)O.[C:39]([O:43][C:44]([NH:46][C:47]1[CH:56]=[CH:55][C:50]([C:51]([O:53][CH3:54])=[O:52])=[CH:49][N:48]=1)=[O:45])([CH3:42])([CH3:41])[CH3:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:39]([O:43][C:44]([N:46]([CH:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH2:18][CH2:17][C:16]([F:38])([F:37])[F:15])[C:47]1[CH:56]=[CH:55][C:50]([C:51]([O:53][CH3:54])=[O:52])=[CH:49][N:48]=1)=[O:45])([CH3:42])([CH3:40])[CH3:41]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2764194Methyl 6-((tert-butoxycarbonyl)amino)nicotinateHCID 866673024,4,4-Trifluoro-1-(4'-(trifluoromethyl)biphenyl-4-yl)butan-1-ol

생성물 1

HCID 86667303Methyl 6-(tert-butoxycarbonyl(4,4,4-trifluoro-1-(4'-(trifluoromethyl)biphenyl-4-yl)butyl)amino)nicotinate수율 21.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Diisopropyl azodicarboxylate (50 μL, 0.25 mmol) was added to a room temperature solution of 4,4,4-trifluoro-1-(4′-(trifluoromethyl)biphenyl-4-yl)butan-1-ol (84 mg, 0.24 mmol), methyl 6-(tert-butoxycarbonylamino)nicotinate (74 mg, 0.29 mmol), and triphenylphosphine (65 mg, 0.25 mmol) in 1.5 mL THF. The resulting solution was stirred overnight at room temperature. The solution was partitioned between dichloromethane and water. The organic layer was dried over MgSO4 and concentrated to give a colorless solid. Purification by silica gel chromatography provided methyl 6-(tert-butoxycarbonyl(4,4,4-trifluoro-1-(4′-(trifluoromethyl)biphenyl-4-yl)butyl)amino)nicotinate (30 mg, 21%) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 8.99-9.01 (m, 1H), 8.17-8.21 (m, 1H), 7.63-7.69 (m, 4H), 7.49-7.54 (m, 3H), 7.39-7.44 (m, 2H), 5.98-6.08 (m, 1H), 3.92 (s, 3H), 2.61-2.74 (m, 1H), 2.39-2.54 (m, 1H), 2.17-2.36 (m, 2H), 1.31 (s, 9H).

후처리

  1. customThe solution was partitioned between dichloromethane and water
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customto give a colorless solid
  5. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-6aa27e755e924972ad72db1b19e6de8b
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933104B2

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