p-Toluenesulphonyl cyanide → 2-Chloro-6-fluoroimidazo[1,2-A]pyridine-3-carbonitrile

HRID 705075ノート

反応式

HRID 705075 の反応式
[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][N:5]2[C:11]=1I.C([Li])CCC.C1(C)C=CC(S([C:27]#[N:28])(=O)=O)=CC=1>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][N:5]2[C:11]=1[C:27]#[N:28]

参加物

5

反応物 3

HCID 87946p-Toluenesulphonyl cyanideHCID 717433442-Chloro-6-fluoro-3-iodoimidazo[1,2-A]pyridineHCID 178418339Butyllithium

生成物 1

HCID 717433462-Chloro-6-fluoroimidazo[1,2-A]pyridine-3-carbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cooled −78° C. solution of the title compound from Example 3 Step A (0.30 g, 1.01 mmol) in tetrahydrofuran (5.06 ml) was added a solution of n-butyllithium in hexanes (1.6 M, 0.696 ml, 1.11 mmol). After 5 minutes, p-toluenesulfonyl cyanide (0.238 g, 1.32 mmol) was added, and the resulting mixture was allowed to slowly warm to room temperature overnight. The resulting mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel (10-50% ethyl acetate in hexanes) to afford the title compound: LCMS m/z 195.88 [M+H]+, 197.86 [M+2+H]+; 1H NMR (500 MHz, CDCl3) δ 8.25 (d, J=2.4 Hz, 1H), 7.69 (dd, J=9.6, 4.8 Hz, 1H), 7.46-7.42 (m, 1H).

後処理

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. custompurified by flash chromatography on silica gel (10-50% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-fce6c14083854af4b7c41a00488cfa21
出典データセット
uspto-grants-2015_11
特許番号
US09173873B2

反応ノート

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