Phosphorus oxychloride → HCID 89925457, compound

HRID 922474Notes

Reaction equation

HRID 922474 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N+:11]([O-])=[CH:10][C:9]=2[C:8]([CH3:21])=[CH:7]1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:10]1[C:9]2[C:8]([CH3:21])=[CH:7][N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:14]=2[CH:13]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 89925444HCID 89925444, compound

Product 1

HCID 89925457HCID 89925457, compound

Procedure

A solution of ethyl 1-(3-methoxypropyl)-3-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate 5-oxide (40 mg) in phosphorus oxychloride (2 mL) was stirred at 100° C. for 1 hours. The reaction solution was concentrated, and the resulting residue was dissolved in ethyl acetate. It was sequentially washed with aqueous saturated sodium hydrogen carbonate solution and saturated saline, and dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=1/1) to give ethyl 4-chloro-1-(3-methoxypropyl)-3-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate [REx(105-6)] (23 mg) as a colorless powder.

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionthe resulting residue was dissolved in ethyl acetate
  3. washIt was sequentially washed with aqueous saturated sodium hydrogen carbonate solution and saturated saline
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-335545e95ba94b1ebc81d1e4d4670d98
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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