HCID 69214722, compound → HCID 69216568, compound

HRID 2053447Notes

Reaction equation

HRID 2053447 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=1)=[O:10].[Cu](C#N)[C:20]#[N:21]>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:20]#[N:21])=[CH:4][C:3]=1[C:9](=[O:10])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 69214722HCID 69214722, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 69216568HCID 69216568, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

A flask charged with (2-amino-5-bromo-phenyl)-(4-ethyl-phenyl)-methanone (0.10 g, 0.32 mmol), copper cyanide (0.0347 g, 0.41 mmol), and 1 mL of DMF was heated at 180° C. for 1 hour in a microwave reactor. The title compound was eluted from a 5 g SPE with 100% DCM to give 0.07 g (81%) of a white solid. 1H NMR (400 MHz, CDCl3) δ 7.84 (d, 1H), 7.58 (d, 2H), 7.50 (dd, 1H), 7.36 (d, 2H), 6.78 (d, 1H), 6.60 (br s, 2H), 2.78 (q, 2H), 1.30 (t, 3H). This was prepared according to example 41. 1H NMR (400 MHz, CD3OD) δ 8.60 (s, 1H), 7.90 (dd, 1H), 7.50 (m, 4H), 7.22 (d, 2H), 6.48 (s, 1H), 2.82 (q, 2H), 1.36 (t, 3H). Mass spectrum (ESI, m/z) calcd. for C21H16N4O 340.1, found 341.1 (M+H).

Workup

  1. washThe title compound was eluted from a 5 g SPE with 100% DCM

Sources & evidence

ORD record
ord-5d1a518413cb474bb42ae5a52d18e85f
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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