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Sodium Carbonate → 1-(4-chloro-1,1'-biphenyl-3-yl)-N-(cyanomethyl)piperidine-2-carboxamide

HRID 1744164
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HRID 1744164 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]2[C:14]([NH:16][CH2:17][C:18]#[N:19])=[O:15])[CH:7]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:20][C:5]1[CH:4]=[CH:3][C:2]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:7][C:6]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([NH:16][CH2:17][C:18]#[N:19])=[O:15]
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 222361681-(5-bromo-2-chlorophenyl)-N-(cyanomethyl)piperidine-2-carboxamide

생성물 1

HCID 222359081-(4-chloro-1,1'-biphenyl-3-yl)-N-(cyanomethyl)piperidine-2-carboxamide

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

A mixture of 1-(5-bromo-2-chlorophenyl)-N-(cyanomethyl)piperidine-2-carboxamide (125 mg, 0.35 mmol), phenylboronic acid (64 mg, 0.53 mmol), PdCl2(dppf) (29 mg, 0.035 mmol) and 2 N Na2CO3 (0.5 mL, 1.1 mmol) in DMF (3.5 mL) was degassed and then heated to 110° C. for 4 h. The mixture was cooled and partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate (3×) and the combined organic layers were dried over Na2SO4 and concentrated. Purification by flash chromatography (50% Et2O/hexanes) afforded 1-(4-chloro-1,1′-biphenyl-3-yl)-N-(cyanomethyl)piperidine-2-carboxamide.

후처리

  1. customwas degassed
  2. temperatureThe mixture was cooled
  3. custompartitioned between water and ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by flash chromatography (50% Et2O/hexanes)

출처 및 근거

ORD 기록
ord-0e35022499b1405f9e7fde2588006015
출처 데이터셋
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07012075B2

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