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

HRID 705075노트

반응식

HRID 705075 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-fce6c14083854af4b7c41a00488cfa21
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173873B2

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