N-bromobutanimide → 5-Bromo-6-(phenylethynyl)-[4,4'-bipyridin]-2-amine

HRID 923667Notes

Reaction equation

HRID 923667 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[N:14]=[C:13]([NH2:15])[CH:12]=[C:11]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:22]N1C(=O)CCC1=O>C(#N)C>[Br:22][C:10]1[C:11]([C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)=[CH:12][C:13]([NH2:15])=[N:14][C:9]=1[C:8]#[C:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1179110016-(Phenylethynyl)-[4,4'-bipyridin]-2-amine

Product 1

HCID 1179032105-Bromo-6-(phenylethynyl)-[4,4'-bipyridin]-2-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-(2-phenylethynyl)-4-(pyridin-4-yl)pyridin-2-amine G1 (93 mg, 0.34 mmol), N-bromosuccinimide (61 mg, 0.34 mmol) and ACN (11 ml) is stirred in the dark at RT for 20 h. The mixture is concentrated in vacuo and the product purified by NP chromatography. Yield: 90 mg (75%). HPLC-MS: M+H=350/352; tR=1.18 min (METHOD—5).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe product purified by NP chromatography

Sources & evidence

ORD record
ord-33f4f517fa3b496e9b0bd75d1ef63a74
Source dataset
uspto-grants-2016_03
Patent number
US09278978B2

Reaction notes

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