HCID 10449285, compound → HCID 22229111, compound

HRID 1744392Notes

Reaction equation

HRID 1744392 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[Sn](C)(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([O:28][CH2:29][CH2:30][CH2:31][OH:32])[CH:22]=[CH:21]2>CN(C=O)C.Cl[Pd-2](Cl)(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:32][CH2:31][CH2:30][CH2:29][O:28][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[C:19]([C:9]1[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:12]=[CH:11][CH:10]=1)=[CH:18][CH:27]=[CH:26]2

Participants

5

Reactant 2

HCID 10449285HCID 10449285, compoundHCID 22229113HCID 22229113, compound

Product 1

HCID 22229111HCID 22229111, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418903HCID 178418903, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To N-tert-butoxycarbonyl-2-trimethylstannylpyrrole (3.0 g) and 6-bromo-2-(3-hydroxypropyloxy)naphthalene (2.55 g) in 20 ml of DMF was added dichloro bis(triphenylphosphino)palladium(II) (64 mg) under an argon atmosphere. The mixture was heated at 70° C. for 16 h. After cooling the mixture was washed with diethyl ether and water. The combined organic layers were dried (MgSO4), filtered, and concentrated. The crude product was purified by column chromatography (silica, hexane/dichloromethane, 2/98, v/v) to give a pure oil in 60% yield [2-(6-(3-hydroxypropyloxy)-naphthyl)-N-tert-butoxycarbonylpyrrole]. To this oil (0.5 g) in 10 ml of DMF was added dropwise phophorusoxychloride (0.42 g) at 0° C. under an argon atmosphere. The mixture was heated at 60° C. for 2 h. After cooling the mixture was neutralized with aqueous sodium hydroxide (1 M) and heated at 80° C. for 1 h. After cooling the precipitate was filtered off and purified by column chromatography (silica, methanol/dichloromethane, 1/99,v/v) to give a 75% yield of 5-formyl-2-(6-(3-chloropropyloxy)-naphthyl)-N—H-pyrrole.

Workup

  1. temperatureAfter cooling the mixture
  2. washwas washed with diethyl ether and water
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica, hexane/dichloromethane, 2/98, v/v)

Sources & evidence

ORD record
ord-5976ee8892c24035b1adc890de592965
Source dataset
uspto-grants-2006_03
Patent number
US07015301B2

Reaction notes

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