Sodium hydride → HCID 49779380, compound

HRID 1773283Notes

Reaction equation

HRID 1773283 reaction equation
[CH:1]1([N:4]2[CH2:17][CH2:16][C:7]3[NH:8][C:9]4[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=4[C:6]=3[CH2:5]2)[CH2:3][CH2:2]1.[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]1([N:4]2[CH2:17][CH2:16][C:7]3[N:8]([CH2:20][C:21]([C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)([OH:22])[CH3:23])[C:9]4[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=4[C:6]=3[CH2:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 123953864-(2-Methyloxiran-2-yl)pyridineHCID 66612137HCID 66612137, compound

Product 1

HCID 49779380HCID 49779380, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-cyclopropyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (500 mg, 2.2 mmol) in DMF (10 mL) was added sodium hydride (264 mg, 6.6 mmol). After stirring for 10 min at RT, 4-(2-methyl-oxiranyl)-pyridine (448 mg, 3.3 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 anhydrous sodium sulfate and concentrated to afford crude material, which was re-crystallized in ether and hexane to yield 1-(2-cyclopropyl-8-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyridin-4-yl)propan-2-ol (600 mg). 1H NMR (CD3OD, TFA salt) d (ppm): 8.62 (d, 2H), 8.18 (d, 2H), 7.20 (s, 1H), 6.95 (d, 1H), 6.80 (d, 1H), 4.50 (m, 1H), 4.40 (s, 2H), 4.0 (m, 1H), 3.70 (m, 1H), 3.30 (m, 3H), 3.10 (m, 1H), 2.36 (s, 3H), 1.78 (s, 3H), 1.20 (m, 4H).

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 anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto afford crude material, which
  8. customwas re-crystallized in ether

Sources & evidence

ORD record
ord-1fd18ae90f8d490089b37d970d26b409
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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