Sodium hydride → HCID 49779379, compound

HRID 1773285Notes

Reaction equation

HRID 1773285 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[NH:10][C:9]3[CH2:12][CH2:13][N:14]([CH3:16])[CH2:15][C:8]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[CH3:19][C:20]1([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[CH2:22][O:21]1>CN(C=O)C>[CH3:1][O:2][C:3]1[C:11]2[N:10]([CH2:19][C:20]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)([OH:21])[CH3:22])[C:9]3[CH2:12][CH2:13][N:14]([CH3:16])[CH2:15][C:8]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 123953864-(2-Methyloxiran-2-yl)pyridineHCID 545884621253640-41-3

Product 1

HCID 49779379HCID 49779379, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-methoxy-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (500 mg, 2.3 mmol) in DMF (10 mL) was added sodium hydride (276 mg, 6.9 mmol) and stirred for 10 min at RT, followed by addition of 4-(2-methyl-oxiranyl)-pyridine (468 mg, 3.4 mmol) 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 material, which was re-crystallized in ether and hexane to yield 1-(6-methoxy-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 (m, 2H), 7.95 (m, 2H), 6.95 (m, 2H), 6.50 (m, 1H), 4.65 (m, 2H), 4.30 (m, 2H), 3.90 (m, 2H), 3.80 (s, 3H), 3.60 (m, 2H), 3.10 (s, 3H), 1.70 (s, 3H).

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 material, which
  8. customwas re-crystallized in ether

Sources & evidence

ORD record
ord-a494a505ab2049f8bcff63430739ba8e
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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