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Cesium carbonate → 4'-[(1S,2R)-2-(2-Hydroxyethyl)cycloprop-1-yl]biphenyl-4-carbonitrile

HRID 515048
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HRID 515048 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@@H:9]2[CH2:11][CH2:12][OH:13])=[CH:4][CH:3]=1.[C:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)#[N:15].C([O-])([O-])=O.[Cs+].[Cs+]>C(O)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:13][CH2:12][CH2:11][C@H:9]1[CH2:10][C@@H:8]1[C:5]1[CH:6]=[CH:7][C:2]([C:19]2[CH:20]=[CH:21][C:16]([C:14]#[N:15])=[CH:17][CH:18]=2)=[CH:3][CH:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 27343264-Cyanophenylboronic acidHCID 684071222-[(1R,2S)-2-(4-Bromophenyl)cycloprop-1-yl]ethanol

생성물 1

HCID 684076744'-[(1S,2R)-2-(2-Hydroxyethyl)cycloprop-1-yl]biphenyl-4-carbonitrile

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매
HCID 3776
Isopropanol
용매

실험 절차

A solution of the product of Example 28E (2-[(1R,2S)-2-(4-bromophenyl)cycloprop-1-yl]ethanol), 4-cyanophenylboronic acid [CAS 126747-14-6] (2 equivalents), Pd(PPh3)2Cl2, and Cs2CO3 in isopropanol under N2 was stirred at reflux overnight. The mixture was partitioned between ethyl acetate and H2O. The organic layer was washed with saturated aqueous NaHCO3 and then with brine. The organic layer was then dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the resulting residue was purified by chromatography on silica gel eluted with 4:1 hexanes/ethyl acetate to provide the title compound.

후처리

  1. temperatureat reflux overnight
  2. customThe mixture was partitioned between ethyl acetate and H2O
  3. washThe organic layer was washed with saturated aqueous NaHCO3
  4. dry with materialThe organic layer was then dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe resulting residue was purified by chromatography on silica gel
  8. washeluted with 4:1 hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-4d5003c5387e48bf9c8ea8063b9ce60a
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09108948B2

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