Sodium hydride → HCID 19010472, compound

HRID 1741668Notes

Reaction equation

HRID 1741668 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=2)[NH:16][CH:15]=1)[C:6]([O:8][CH3:9])=[O:7].Br[CH2:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][C:32]([Cl:38])=[CH:33][CH:34]=2)[N:29]=1.[H-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=2)[N:16]([CH2:27][C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][C:32]([Cl:38])=[CH:33][CH:34]=3)[N:29]=2)[CH:15]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 102441602-(Bromomethyl)-7-chloroquinolineHCID 114732633-(2-Methoxy-4-methoxycarboxybenzyl)-5-nitroindole

Product 1

HCID 19010472HCID 19010472, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of the methyl 3-methoxy-4-(5-nitroindol-3-ylmethyl)benzoate (312 mg, 0.92 mmol) (J. Med. Chem. 1990, 33, 1781-1790) and 2-bromomethyl-7-chloroquinoline (225 mg, 0.88 mmol) in DMF (3 ml) at 0° C. was added 50% NaH (48 mg, 1.04 mmol). After stirring at 0° C. for 1 hr, ice was added to the reaction mixture. When the ice had melted the resultant solid was filtered, dried and swished with Et2O to afford the title compound (311 mg).

Workup

  1. additionice was added to the reaction mixture
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-93bd61f4d347443589c55992c4a18a5c
Source dataset
uspto-grants-1994_08
Patent number
US05334597

Reaction notes

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