Cesium fluoride → Tert-butyl 4-((4'-chlorobiphenyl-2-yl)methyl)piperazine-1-carboxylate

HRID 731556ノート

反応式

HRID 731556 の反応式
Br[C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.[F-].[Cs+]>COCCOC>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=2[CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 25953Cesium fluorideHCID 742994-Chlorophenylboronic acidHCID 20754660Tert-butyl 4-(2-bromobenzyl)piperazine-1-carboxylate

生成物 1

HCID 22662065Tert-butyl 4-((4'-chlorobiphenyl-2-yl)methyl)piperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

A solution of EXAMPLE 22A (5.82 g, 16.394 mmol) in DME (80 mL) was treated with 4-chlorophenylboronic acid (3.089 g, 19.673 mmol), CsF (7.476 g, 49.182 mmol) and (Ph3P)2Pd(OAc)2 (1.228 g, 1.639 mmol), heated to reflux for 4 hours, and filtered. The filtrate was partitioned between aqueous NaHCO3 and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined extracts were dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel column chromatography with 15% ethyl acetate/hexane to provide the desired product. MS (ESI) m/e 386, 388 (M+H)+.

後処理

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. filtrationfiltered
  4. customThe filtrate was partitioned between aqueous NaHCO3 and ethyl acetate
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialthe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography with 15% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-c073f31f8f5141d58bab2a75e8cd5627
出典データセット
uspto-grants-2009_09
特許番号
US07585858B2

反応ノート

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