Triphenylarsine → 5-isoquinolin-4-yl-1H-pyrrole-2-carboxylic acid methyl ester

HRID 985611Notes

Reaction equation

HRID 985611 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7](Br)=[CH:8][CH:9]=1)=[O:4].C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[Sn](C)(C)[C:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[N:34][CH:33]=1>CN1C(=O)CCC1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]([C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=[N:34][CH:33]=2)=[CH:8][CH:9]=1)=[O:4]

Participants

6

Reactant 3

HCID 11773TriphenylarsineHCID 11600885Methyl 5-bromo-1H-pyrrole-2-carboxylateHCID 127591074-(Trimethylstannyl)isoquinoline

Product 1

HCID 697453555-isoquinolin-4-yl-1H-pyrrole-2-carboxylic acid methyl esterYield 55%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5-Bromo-1H-pyrrole-2-carboxylic acid methyl ester (1.49 mmol, 0.30 g, prepared according to the procedure described in Method 4 of Example 2) in NMP (10 ml) was treated with triphenylarsine (0.30 mmol, 91 mg), tris(dibenzylideneacetone) dipalladium(0) (0.07 mmol, 68 mg), and 4-(trimethylstannyl)-isoquinoline (2.22 mmol, 0.65 g), then heated to reflux under an argon atmosphere overnight. The resulting mixture was concentrated under reduced pressure, then purified by silica gel chromatography to provide 0.21 g (55%) of 5-isoquinolin-4-yl-1H-pyrrole-2-carboxylic acid methyl ester. 1H NMR (CDCl3) δ 9.81 (1H, br s), 9.35 (1H, s), 8.66 (1H, s), 8.31 (1H, d, J=8.5), 8.10 (1H, d, J=8.1), 7.91 (1H, t, J=15.2), 7.79 (1H, t, J=15.2), 7.11 (1H, dd, J=3.8, 2.5), 6.64 (1H, dd, J=3.7, 2.7), 3.90 (3H, s).

Workup

  1. temperatureheated
  2. temperatureto reflux under an argon atmosphere overnight
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-fd6a3cbfe1a74ea69f5591526f29e6e9
Source dataset
uspto-grants-2005_03
Patent number
US06872745B2

Reaction notes

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