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

HRID 731556노트

반응식

HRID 731556 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-c073f31f8f5141d58bab2a75e8cd5627
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585858B2

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