Sodium Bicarbonate → tert-butyl 2-(1-(4-bromophenyl)-2-(2-(2-chlorophenyl)propan-2-yl)-1H-imidazol-4-yl)pyrrolidine-1-carboxylate

HRID 1673025ノート

反応式

HRID 1673025 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[NH:20])[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.I[CH2:22][C:23]([CH:25]1[CH2:29][CH2:28][CH2:27][N:26]1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=O.C([O-])(O)=O.[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:22]=[C:23]([CH:25]3[CH2:29][CH2:28][CH2:27][N:26]3[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[N:20]=[C:9]2[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])([CH3:12])[CH3:11])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 57458742HCID 57458742、化合物HCID 178449869HCID 178449869、化合物

生成物 1

HCID 67339382tert-butyl 2-(1-(4-bromophenyl)-2-(2-(2-chlorophenyl)propan-2-yl)-1H-imidazol-4-yl)pyrrolidine-1-carboxylate収率 5.5%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of N-(4-bromophenyl)-2-(2-chlorophenyl)-2-methylpropanimidamide (3.51 g, 10 mmol) in 60 mL dioxane was added tert-butyl 2-(2-iodoacetyl)pyrrolidine-1-carboxylate (3.38 g, 10 mmol) and NaHCO3 (2.5 g, 30 mmol). The mixture was heated to reflux with stirring for 2 days. The reaction was monitored by LC/MS. The reaction mixture was cooled and filtered over celite. The crude mixture was initially purified by silica gel column chromatography. The fraction containing the desired product was further purified by prep HPLC, affording 300 mg (5.5%) of tert-butyl 2-(1-(4-bromophenyl)-2-(2-(2-chlorophenyl)propan-2-yl)-1H-imidazol-4-yl)pyrrolidine-1-carboxylate. 1H NMR (CD3OD): δ 1.4 (m, 10H), 1.6 (m, 3H,), 1.8 (m, 1H), 1.9-2.3 (m, 5H), 3.4 (m, 1H), 3.6 (m, 1H) 4.6 (m, 1H), 6.9 (m, 3H), 7.05 (m, 1H), 7.2 (m, 2H), 7.25 (m, 1H), 7.50 (m, 2H); LC/MS M+H 544 (observed).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered over celite
  5. customThe crude mixture was initially purified by silica gel column chromatography
  6. additionThe fraction containing the desired product
  7. customwas further purified by prep HPLC

出典と根拠

ORDレコード
ord-110048fcb3f9474ca3963844fa53457b
出典データセット
uspto-grants-2011_08
特許番号
US07998995B2

反応ノート

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