N-Methyl dicyclohexylamine → HCID 89922748, 화합물

HRID 921840노트

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HRID 921840 반응식
[NH2:1][C:2]1[C:3]([Cl:11])=[CH:4][C:5](Br)=[C:6]([CH:9]=1)[C:7]#[N:8].C1(N(C)C2CCCCC2)CCCCC1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1C)(C)(C)C.[CH2:48]([OH:52])[CH2:49][CH:50]=[CH2:51]>CC#N.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C=O)C>[NH2:1][C:2]1[C:3]([Cl:11])=[CH:4][C:5]([CH2:51][CH2:50][CH2:49][CH:48]=[O:52])=[C:6]([CH:9]=1)[C:7]#[N:8]

참가 물질

9

반응물 4

HCID 24210N-Methyl dicyclohexylamineHCID 693893-Buten-1-olHCID 27349372-(Di-tert-butylphosphino)-2'-methyl-1,1'-biphenylHCID 532162295-Amino-2-bromo-4-chlorobenzonitrile

생성물 1

HCID 89922748HCID 89922748, 화합물수율 23.4%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

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온도
60 °C

실험 절차

5-amino-2-bromo-4-chlorobenzonitrile (4 g, 17.28 mmol) and N-cyclohexyl-N-methylcyclohexanamine (5.55 mL, 25.9 mmol) were combined in a 250 ml flask and 2 ml of DMF was added. The flask was evacuated and backfilled with Ar 4×. A suspension of Pd2 (dba)3 (0.316 g, 0.346 mmol) and di-tert-butyl(2′-methyl-[1,1′-biphenyl]-2-yl)phosphine (0.324 g, 1.037 mmol) in CH3CN (32 mL) was heated at 60° C. for 1 min until the solids dissolved and then cooled to room temperature. The solution was added to the flask by syringe, and then but-3-en-1-ol (1.933 mL, 22.46 mmol) was added. The reaction was heated at 90° C. for 45 min. The reaction was cooled to room temperature and diluted with H2O, extracting 3× with EtOAc. The organic layers were dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography (0-70% EtOAc/Hex; 330 g column). 5-amino-4-chloro-2-(4-oxobutyl)benzonitrile (0.9 g) was obtained as yellow foam.

후처리

  1. customThe flask was evacuated
  2. dissolutiondissolved
  3. temperaturecooled to room temperature
  4. additionThe solution was added to the flask by syringe
  5. temperatureThe reaction was heated at 90° C. for 45 min
  6. temperatureThe reaction was cooled to room temperature
  7. extractionextracting 3× with EtOAc
  8. dry with materialThe organic layers were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe material was purified by flash column chromatography (0-70% EtOAc/Hex; 330 g column)

출처 및 근거

ORD 기록
ord-0f4bb32eddc3463780d0ae6a7a871ff0
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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