Sodium hydride → HCID 59455242, compound

HRID 1773260Notes

Reaction equation

HRID 1773260 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:17][CH2:16][C:7]2[NH:8][C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1.[F:18][C:19]1[CH:20]=[C:21]([C:27]2([CH3:30])[CH2:29][O:28]2)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]>CN(C=O)C>[CH3:3][N:4]1[CH2:17][CH2:16][C:7]2[N:8]([CH2:30][C:27]([C:21]3[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:19]([F:18])[CH:20]=3)([OH:28])[CH3:29])[C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 59455004HCID 59455004, compound

Product 1

HCID 59455242HCID 59455242, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A flask was charged with sodium hydride 60% (461 mg, 1.15 mmol) in DMF and stirred at RT for 10 min. 2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.76 g, 3.8 mmol) was added and the mixture stirred at RT for 1 h. 2-(3-Fluoro-4-methoxyphenyl)-2-methyloxirane (1 g, 5.4 mmol) was added and the mixture stirred at RT overnight. Ice water was added and the mixture extracted with EtOAc (3×). The combined organic layers were washed with water (4×) and concentrated, followed by purification of the product on silica gel (#100-200 mesh) using 0-5% MeOH:DCM as eluent. 1HNMR (DMSO, Oxalate salt) d (ppm): 7.30 (m, 3H), 7.18 (s, 1H), 7.10 (d, 1H), 6.90 (d, 1H), 4.30 (m, 2H), 4.18 (d, 1H), 4.05 (d, 1H), 3.80 (s, 3H), 3.60 (m, 2H), 3.0 (m, 2H), 2.80 (s, 3H), 2.35 (s, 3H), 1.70 (m, 1H), 1.40 (s, 3H).

Workup

  1. stirringthe mixture stirred at RT for 1 h
  2. stirringthe mixture stirred at RT overnight
  3. extractionthe mixture extracted with EtOAc (3×)
  4. washThe combined organic layers were washed with water (4×)
  5. concentrationconcentrated
  6. customfollowed by purification of the product on silica gel (#100-200 mesh)

Sources & evidence

ORD record
ord-6afb8563b8a7411db49e671e7b853d40
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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