Dimethylformamide → 7-[3-(4-Methoxy-tetrahydro-pyran-4-yl)-phenylsulfanyl]-1,2-dihydro-imidazo[1,2-a]quinoline

HRID 2075672Notes

Reaction equation

HRID 2075672 reaction equation
[CH2:1]1[N:5]2[C:6]3[C:11]([CH:12]=[CH:13][C:4]2=[N:3][CH2:2]1)=[CH:10][C:9]([S:14][C:15]1[CH:16]=[C:17]([C:21]2([OH:27])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:18]=[CH:19][CH:20]=1)=[CH:8][CH:7]=3.[H-].[Na+].[CH3:30]N(C=O)C>IC>[CH3:30][O:27][C:21]1([C:17]2[CH:16]=[C:15]([S:14][C:9]3[CH:10]=[C:11]4[C:6](=[CH:7][CH:8]=3)[N:5]3[CH2:1][CH2:2][N:3]=[C:4]3[CH:13]=[CH:12]4)[CH:20]=[CH:19][CH:18]=2)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 58257754HCID 58257754, compound

Product 1

HCID 589265167-[3-(4-Methoxy-tetrahydro-pyran-4-yl)-phenylsulfanyl]-1,2-dihydro-imidazo[1,2-a]quinoline

Reagents, catalysts & solvents 1

HCID 6328Methyl iodideCatalyst

Procedure

To a solution of 2c (42 mg, 0.11 mmol) in DMF was added sodium hydride (5 mg, 0.12 mmol). Iodomethane (one drop) was added, and the mixture was stirred at room temperature for 5 hours. The reaction was quenched with water, extracted with EtOAc, and purified by preparative HPLC to give the desired product, 2d.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-e203a1947ade42488940c3a34bafb33f
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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