Dimethylamine → HCID 69271636, compound

HRID 751536Notes

Reaction equation

HRID 751536 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[C:13](=[O:31])[NH:14][C:15](=[O:30])[C:16]=2[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:26][CH2:27][CH2:28]Br)[CH:18]=2)[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1.[CH3:32][NH:33][CH3:34]>CN1CCCC1=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[C:13](=[O:31])[NH:14][C:15](=[O:30])[C:16]=2[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:26][CH2:27][CH2:28][N:33]([CH3:34])[CH3:32])[CH:18]=2)[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 69270149HCID 69270149, compound

Product 1

HCID 69271636HCID 69271636, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve 3-(5-methoxybenzofur-7-yl)-4-[1-(3-hydroxypropyl)-1H-indol-3-yl]pyrrole-2,5-dione (0.058 g, 0.118 mmol) in 10 mL dichloromethane. Add carbon tetrabromide (0.077 g, 1 equivalent) and triphenyl phosphine (0.061 g, 1 equivalent). Stir for 10 min, add another equivalent of both reagents. Stir 10 min then dilute with dichloromethane and wash with water followed by brine. Dry over magnesium sulfate then filter and concentrate. Purification by column chromatography (2% methanol:dichloromethane) affords the 3-(5-methoxybenzofur-7-yl)-4-[1-(3-bromopropyl)-1H-indol-3-yl)pyrrole-2,5-dione. 3-(5-Methoxybenzofur-7-yl)-4-[1-(3-bromopropyl)-1H-indol-3-yl]pyrrole-2,5-dione is dissolved in 1.5 mL 1-methyl-2-pyrrolidinone and add dimethylamine (2M solution in tetrahydrofuran, 0.3 mL, 5 equivalents). Heat to 60° C. for 16 hrs. Extract with ethyl acetate versus water, concentrate organic layer. Redissolve in a minimal amount of methanol and load onto an SCX™ Varian column (pretreated with a 5% acetic acid: methanol solution). Wash with methanol and ethyl acetate to remove impurities, flush with 2M ammonia methanol to recover product. ES(M++H)444.0.

Workup

  1. extractionExtract with ethyl acetate versus water
  2. concentrationconcentrate organic layer
  3. dissolutionRedissolve in a minimal amount of methanol and load onto an SCX™ Varian column (
  4. washWash with methanol and ethyl acetate
  5. customto remove impurities
  6. customflush with 2M ammonia methanol
  7. customto recover product

Sources & evidence

ORD record
ord-80e62deff1614fbf8c5297e2440dd2d0
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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