Water → HCID 131734966, compound

HRID 922471Notes

Reaction equation

HRID 922471 reaction equation
COCCC[N:6]1[C:14]2[CH:13]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:11]=[CH:10][C:9]=2[CH:8]=[CH:7]1.BrN1C(=O)CC[C:22]1=[O:27].O.Cl[CH2:30]Cl>>[CH3:30][O:27][CH2:22][CH2:19][CH2:18][O:17][C:15]([C:12]1[N:11]=[CH:10][C:9]2[CH:8]=[CH:7][NH:6][C:14]=2[CH:13]=1)=[O:16]

Participants

5

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 89925499HCID 89925499, compound

Product 1

HCID 131734966HCID 131734966, compound

Procedure

To a solution of ethyl 1-(3-methoxypropyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (2.00 g) in dichloromethane (40 mL) was added N-bromosuccinimide (1.49 g) under ice-cooling, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added water, and the mixture was extracted with chloroform. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→4/1) to give ethyl 3-bromo-1-(3-methoxypropyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate [REx(105-3)] (2.12 g) as a yellow oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→4/1)

Sources & evidence

ORD record
ord-96570c1f7b1e441599b54b641b4c6591
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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