Sodium hydride → HCID 49779378, 화합물

HRID 1773287노트

반응식

HRID 1773287 반응식
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH2:16][N:15]([CH3:17])[CH2:14][CH2:13][C:9]=3[NH:10][C:11]=2[CH:12]=1)([CH3:3])[CH3:2].[H-].[Na+].[CH3:20][C:21]1([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH2:23][O:22]1>CN(C=O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH2:16][N:15]([CH3:17])[CH2:14][CH2:13][C:9]=3[N:10]([CH2:20][C:21]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)([OH:22])[CH3:23])[C:11]=2[CH:12]=1)([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 123953864-(2-Methyloxiran-2-yl)pyridineHCID 66611743HCID 66611743, 화합물

생성물 1

HCID 49779378HCID 49779378, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 7-isopropyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (500 mg, 2.1 mmol) in DMF (10 mL) was added sodium hydride (252 mg, 6.3 mmol). After stirring for 10 min at RT, 4-(2-methyl-oxiranyl)-pyridine (444 mg, 3.2 mmol) was added and stirring continued for another 16 h. The reaction mixture was poured into ice water and extracted with EtOAc. The organic layer was washed with water, dried over sodium sulfate and concentrated to afford crude product which was re-crystallized in ether and hexane to yield 1-(7-isopropyl-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyridin-4-yl)propan-2-ol. 1H NMR (CD3OD, TFA salt) d (ppm): 8.60 (d, 2H), 8.05 (d, 2H), 7.25 (d, 1H), 6.90 (d, 1H), 6.78 (s, 1H), 4.65 (m, 1H), 4.42 (s, 2H), 4.30 (m, 1H), 3.90 (m, 1H), 3.60 (m, 2H), 3.30 (m, 1H), 3.10 (s, 3H), 2.85 (m, 1H), 1.80 (s, 3H), 1.18 (m, 6H).

후처리

  1. stirringstirring
  2. waitcontinued for another 16 h
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto afford crude product which
  8. customwas re-crystallized in ether

출처 및 근거

ORD 기록
ord-a7dde935e5a6425e94e39902455a6d1d
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255094B2

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