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Chlorosuccinimide → Tert-butyl 4-(3-chloroimidazo[1,5-a]pyridin-7-yl)piperidine-1-carboxylate

HRID 1487934
ノート
印刷プレビュー

反応式

HRID 1487934 の反応式
[CH:1]1[N:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)=[CH:6][C:5]=12.[Cl:23]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O>[Cl:23][C:1]1[N:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)=[CH:6][C:5]=12.[Cl:23][C:3]1[N:4]2[CH:9]=[CH:8][C:7]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)=[CH:6][C:5]2=[CH:1][N:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 31398ChlorosuccinimideHCID 90033879Tert-butyl 4-(imidazo[1,5-a]pyridin-7-yl)piperidine-1-carboxylate2 回

生成物 2

HCID 90029531Tert-butyl 4-(3-chloroimidazo[1,5-a]pyridin-7-yl)piperidine-1-carboxylate収率 34%HCID 90066730Tert-butyl 4-(1-chloroimidazo[1,5-a]pyridin-7-yl)piperidine-1-carboxylate収率 24%

試薬・触媒・溶媒 2

HCID 5943
Carbon Tetrachloride
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

Into a 25-mL round-bottom flask, was placed a solution of. tert-butyl 4-(imidazo[1,5-a]pyridin-7-yl)piperidine-1-carboxylate (compound 39.4, 170 mg, 0.56 mmol) in CCl4 (3 mL). N-Chlorosuccinimide (75 mg, 0.56 mmol) was added and the resulting mixture was stirred for 5 h at room temperature. The mixture was diluted with EtOAc (30 mL) and washed with brine (3×20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by preparative TLC with ethyl acetate/petroleum ether (1/1) to yield 45 mg (24%) of tert-butyl 4-(1-chloroimidazo[1,5-a]pyridin-7-yl)piperidine-1-carboxylate (compound 68.1) as a yellow solid and 64 mg (34%) of tert-butyl 4-(3-chloroimidazo[1,5-a]pyridin-7-yl)piperidine-1-carboxylate (compound 68.2) as a yellow solid.

後処理

  1. customInto a 25-mL round-bottom flask, was placed
  2. washwashed with brine (3×20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative TLC with ethyl acetate/petroleum ether (1/1)

出典と根拠

ORDレコード
ord-bd56d03b913648189d3bc66b5052a66e
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09428502B2

反応ノート

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