Sodium hydride → HCID 49779378, compound

HRID 1773287Notes

Reaction equation

HRID 1773287 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 49779378HCID 49779378, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a7dde935e5a6425e94e39902455a6d1d
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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