Barium hydroxide, octahydrate → 1-(1-Ethylpropyl)-7-mesityl-4-methyl-1H-pyrrolo[3,2-c]quinoline

HRID 890230Notes

Reaction equation

HRID 890230 reaction equation
[CH2:1]([CH:3]([N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][C:14](I)=[CH:13][C:12]=3[N:11]=[C:10]([C:20]3C(C)=CC(C)=CC=3C)[C:9]=2[CH:8]=[CH:7]1)[CH2:4][CH3:5])[CH3:2].[C:29]1([CH3:41])[CH:34]=[C:33]([CH3:35])[CH:32]=[C:31]([CH3:36])[C:30]=1OB(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>COC(OC)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([CH:3]([N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][C:14]([C:30]4[C:31]([CH3:36])=[CH:32][C:33]([CH3:35])=[CH:34][C:29]=4[CH3:41])=[CH:13][C:12]=3[N:11]=[C:10]([CH3:20])[C:9]=2[CH:8]=[CH:7]1)[CH2:4][CH3:5])[CH3:2]

Participants

7

Reactant 3

HCID 17749109Barium hydroxide, octahydrateHCID 22237855Mesitylboric acidHCID 222497701-(1-ethylpropyl)-7-iodo-4-mesityl-1H-pyrrolo[3,2-c]quinoline

Product 1

HCID 222496751-(1-Ethylpropyl)-7-mesityl-4-methyl-1H-pyrrolo[3,2-c]quinolineYield 51%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 107951,1-DimethoxyethaneSolvent

Procedure

A solution of 1-(1-ethylpropyl)-7-iodo-4-mesityl-1H-pyrrolo[3,2-c]quinoline (32 mg, 0.09 mmol), mesitylboric acid (17 mg, 0.10 mmol), Pd(PPh3)4 (5 mg, 4.23×10−3 mmol) and barium hydroxide octahydrate (40 mg, 0.13 mmol) in 2,2-dimethoxyethane (6.0 mL) and water (1.0 mL) was stirred at 80° C. for one day. After filtering through Celite, the filtrate was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane), to give the title compound (17 mg) as white crystals.

Workup

  1. filtrationAfter filtering through Celite
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9447b5679958473381d18bbc00f8cbd6
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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