4-(Trimethylsilyl)phenylboronic Acid (contains varying amounts of Anhydride) → 1-(4-Trimethylsilanyl-phenyl)-isoquinoline

HRID 2243561Notes

Reaction equation

HRID 2243561 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C[Si](C)(C)C)(C)(C)C>[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.O1CCOCC1>[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][N:16]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 17104-(Trimethylsilyl)phenylboronic Acid (contains varying amounts of Anhydride)HCID 10796Cesium carbonateHCID 140539Isoquinoline, 1-chloro-HCID 12583313Di-tert-butyl-trimethylsilylmethyl-phosphane

Product 1

HCID 252598331-(4-Trimethylsilanyl-phenyl)-isoquinoline

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

15.0 g (0.07727 mol) of 4-trimethylsilyl-phenylboronic acid, 10.11 g (0.0618 mol) 1-chloro-isoquinoline, 15.11 g (0.0464 mol) of cesium carbonate, 0.71 g (0.000775 mol) of tris(dibenzylideneacetone) dipalladium (0), 0.43 g (0.00185 mol) of di-tert-butyl-trimethylsilylmethyl-phosphane and 100 ml of dioxane were stirred at room temperature for 12 hr. The reaction mixture was filtered and the solvent was removed under vacuum. The resulting mixture was purified by chromatography on silica gel using petroleum ether/ethyl ether (10/0.5) as eluent. Yield of 1-(4-trimethylsilanyl-phenyl)-isoquinoline was 10.63 g (62%) as a colorless solid with m.p. 93.45° C. 1H NMR (CDCl3) 0.30 (s, 9H, Me3Si), 7.45-7.70 (m, 7H, arom-H), 7.85 (s, 1H, arom-H), 8.15 (s, 1H, arom-H), 8.51 (s, 1H, arom-H). Anal. Found: C, 77.68; H, 6.95; N, 4.97.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under vacuum
  3. customThe resulting mixture was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c991dd3eefa34ea99951ca3cfafd0200
Source dataset
uspto-grants-2010_03
Patent number
US07675228B2

Reaction notes

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