Cesium carbonate → {[6-(5-Phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetonitrile

HRID 456820Notes

Reaction equation

[C:1]1([C:7]2[NH:11][C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[CH:18]=[C:17]([OH:22])[CH:16]=[CH:15]4)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:24][C:25]#[N:26].C(=O)([O-])[O-].[Cs+].[Cs+]>>[C:1]1([C:7]2[NH:11][C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[CH:18]=[C:17]([O:22][CH2:24][C:25]#[N:26])[CH:16]=[CH:15]4)=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 11534Bromoacetonitrile

HCID 184390376-(5-phenyl-1H-pyrrol-2-yl)-2-naphthol

Product 1

HCID 18439038{[6-(5-Phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetonitrile

Procedure

In a similar manner as described in step 6 of Example 1, the title compound was prepared from 6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthol (0.285 g, 1.00 mmol), prepared in step 5 of Example 1, bromoacetonitrile (0.144 g, 1.20 mmol) and cesium carbonate (1.63 g, 5.00 mmol) with the exception that the reaction was complete after 2 hours at ambient temperature. The isolated tan solids (0.323 g, 100%) were used without further purification, mp 141.5–142.5° C. Elemental Analysis for C22H16N2O Calc'd: C, 81.46; H, 4.97; N, 8.64. Found: C, 80.37; H, 4.93; N,

Workup

customThe isolated tan solids (0.323 g, 100%) were used without further purification, mp 141.5–142.5° C

Sources & evidence

ORD record: ord-030dda6b1fb94fbdb4baddc9942284c5
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186749B2

Reaction notes

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