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Potassium Phosphate, Tribasic → 2-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-4-phenyl-1H-imidazole

HRID 1627330
ノート
印刷プレビュー

反応式

HRID 1627330 の反応式
Br[C:2]1[N:3]=[C:4]([S:25][CH2:26][C:27]2[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:34])[N:5]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[C:6]=1[C:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)([CH3:9])[CH3:8].[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.COC1C=CC=CC=1P(C1C=CC=CC=1OC)C1C=CC=CC=1OC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:34][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]([F:33])[C:27]=1[CH2:26][S:25][C:4]1[N:5]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[C:6]([C:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)([CH3:9])[CH3:8])=[C:2]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 78464Tris(2-methoxyphenyl)phosphineHCID 866622414-bromo-2-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

生成物 1

HCID 667400402-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-4-phenyl-1H-imidazole
収率 17.1%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 19096565Water ethanol溶媒

実験手順

A mixture of 4-bromo-2-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (100 mg, 0.166 mmol), phenylboronic acid (40.5 mg, 0.332 mmol), Pd(OAc)2 (2 mg, 0.008 mmol), tris(2-methoxyphenyl)phosphine (6 mg, 0.017 mmol), and K3PO4 (106 mg, 0.498 mmol) in EtOH—H2O (3 mL, 10:1 v/v) was refluxed overnight. The reaction mixture was filtered through Celite™. The filtrate was concentrated in vacuo, dissolved in DCM (5 mL) and washed with H2O (5 mL). The organic layer was dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (Hex/EtOAc=9:1) to give the title product (17 mg, 17%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.23 (s, 6H), 4.57 (s, 2H), 6.10 (m, 2H), 6.30 (t, 2H), 6.50 (dd, 1H), 6.75 (m, 1H), 6.80 (d, 1H), 6.85 (dd, 1H), 7.19 (m, 1H), 7.25 (t, 2H), 7.70 (s, 1H), 7.71 (s, 1H); MS (EI) m/z 601 [M+H]+.

後処理

  1. temperaturewas refluxed overnight
  2. filtrationThe reaction mixture was filtered through Celite™
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutiondissolved in DCM (5 mL)
  5. washwashed with H2O (5 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography (Hex/EtOAc=9:1)

出典と根拠

ORDレコード
ord-efb42d875bbc4510aa4d9a1dbb67d81f
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785488B2

反応ノート

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