N-bromobutanimide → 3-Bromo-1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine

HRID 1969630ノート

反応式

HRID 1969630 の反応式
[CH:1]1([C:7]2[N:11]3[C:12]4[CH:18]=[CH:17][N:16]([S:19]([C:22]5[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=5)(=[O:21])=[O:20])[C:13]=4[N:14]=[CH:15][C:10]3=[CH:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C(=O)N([Br:36])C(=O)C1>C1COCC1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Br:36][C:9]1[N:8]=[C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[N:11]2[C:12]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:20])=[O:21])[C:13]=3[N:14]=[CH:15][C:10]=12

参加物

6

反応物 2

HCID 67184N-bromobutanimideHCID 580099171-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine

生成物 1

HCID 583822553-Bromo-1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine収率 85.1%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.27 g, 0.67 mmol, prepared using Q from Preparation #13, Lawesson's reagent, and mercury(II) acetate) in THF (10 mL) at about 0° C. was added a solution of NBS (0.12 g, 0.672 mmol) in THF (2 mL). After about 30 min, the reaction mixture was diluted with EtOAc (20 mL) and saturated aqueous NaHCO3 (20 mL). The organic layer was separated, concd in vacuo, and purified by chromatography on silica gel (40 g) eluting with EtOAc:DCM:heptane (1:1:2) to provide 3-bromo-1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.27 g 83%) as a tan solid: LC/MS (Table 1, Method a) Rt=3.12 min; MS m/z 473, 475 (1:1) (M+H)+.

後処理

  1. customThe organic layer was separated
  2. customconcd in vacuo, and purified by chromatography on silica gel (40 g)
  3. washeluting with EtOAc:DCM:heptane (1:1:2)

出典と根拠

ORDレコード
ord-8d30041b43334f3b84430ec9ef7b1dd0
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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