Ammonium Chloride → HCID 54212301, 화합물

HRID 343558

반응식

HRID 343558 반응식
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[CH:23])[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:25]1[S:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=1.[Cl-].[NH4+]>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:30]([C:27]1[S:26][C:25]([C:23]#[C:22][C:15]2([C:9]3[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH:8]=3)[CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH2:20]2)=[CH:29][CH:28]=1)#[N:31]

참가 물질

7

반응물 3

HCID 25517Ammonium ChlorideHCID 35950595-Bromothiophene-2-carbonitrileHCID 10828930HCID 10828930, 화합물

생성물 1

HCID 54212301HCID 54212301, 화합물수율 20.4%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8471Triethylamine용매

실험 절차

To a solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethynyl-cyclohexan-1-one (0.22 g, 0.7 mmol) and 2-bromo-5-cyanothiophene (0.13 g, 0.7 mmol) in triethylamine (5 mL) under an argon atmosphere were added tetrakis(triphenylphosphine)palladium(0) (0.034 g, 4%) and copper(I) iodide (0.007 g, 6%), and the mixture was heated at 85°-90° C. for 2 h. Ammonium chloride was added and the mixture was extracted three times with dichloromethane, was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 2:8 ethyl acetate:hexanes, provided 4-(2-cyanothien-5-ylethynyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (0.06 g, 18%). This was combined with product (0.017 g) obtained in a second, similar reaction and was triturated from dichloromethane-hexanes to provide a white solid, mp 106°-107° C. Anal. (C25H25NO3S.0.5 H2O) calcd: C, 70.07; H, 6.11; N, 3.27; found: C, 70.15; H, 5.84; N, 3.32.

후처리

  1. temperaturethe mixture was heated at 85°-90° C. for 2 h
  2. extractionthe mixture was extracted three times with dichloromethane
  3. dry with materialwas dried (magnesium sulfate)
  4. customwas evaporated
  5. customPurification by flash chromatography
  6. washeluting with 2:8 ethyl acetate

출처 및 근거

ORD 기록
ord-8bffe52f6c2d4fe195a0f85c24515d2f
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05861421

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