Triethylamine → HCID 57714144, 화합물

HRID 1163015노트

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HRID 1163015 반응식
Br[C:2]1[C:3]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[Cl:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]#[CH:28])=[CH:21][CH:20]=1.C(N(CC)CC)C.CCOC(C)=O>CN(C=O)C.[Cu]I.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>[Cl:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]#[C:28][C:2]2[C:3]([NH:10][CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=2)=[CH:21][CH:20]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 107498961-(Chloromethyl)-4-(2-propyn-1-yloxy)benzeneHCID 17968181HCID 17968181, 화합물

생성물 1

HCID 57714144HCID 57714144, 화합물수율 21%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
65 °C

실험 절차

5-Bromo-4-cyclohexylamino-pyrimidine-2-carbonitrile (0.19 mmol) and chloromethyl-4-prop-2-ynyloxy-benzene (0.22 mmol) in DMF (5 ml) are treated with triethylamine (0.56 mmol), copper (I) iodide (0.019 mmol), and dichlorobis(triphenylphosphine)palladium(II) (0.0093 mmol) at room temperature. The mixture is stirred for 2 h at 65° C., poured into an ice water, extracted with AcOEt. The organic layer is washed with brine, dried over magnesium sulfate and concentrated. The crude product is purified by silica gel column chromatography to give the product in 21% yield. Rf=0.75 (n-hexanes:AcOEt=1:2). 1H-NMR (400 MHz, CDCl3) δ 1.02-1.48 (m, 5H), 1.57-1.78 (m, 3H), 1.80-1.98 (m. 2H), 3.94-4.04 (m, 1H), 4.61 (s, 2H), 5.03 (s, 2H), 5.38 (d, 1H), 7.04 (d, 2H), 7.41 (d, 2H), 8.21 (s, 1H).

후처리

  1. extractionextracted with AcOEt
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel column chromatography
  6. customto give the product in 21% yield

출처 및 근거

ORD 기록
ord-44ddf877398343fbacde0f1d1c250409
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820818B2

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