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2-Bromopyrimidine → 4-Pyrimidin-2-ylethynyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 1038043
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HRID 1038043 반응식
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]#[CH:22])[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>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.[Cu]I>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]#[C:22][C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 783452-Bromopyrimidine2회HCID 15550481tert-Butyl 4-ethynylpiperidine-1-carboxylate

생성물 1

HCID 669398774-Pyrimidin-2-ylethynyl-piperidine-1-carboxylic acid tert-butyl ester수율 8%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476
HCID 178418476, 화합물
촉매

실험 절차

To a suspension of 2-bromopyrimidine (175 mg, 1.1 mmols), dichlorobis(triphenylphosphine)palladium(II) (35 mg, 0.05 mmols) and CuI (10 mg, 0.05 mmols) was added a solution of 4-ethynyl-piperidine-1-carboxylic acid tert-butyl ester (209 mg, 1 mmol). The mixture was stirred overnight, filtered through Celite, concentrated. The residue was partitioned between ethyl acetate and water, organic layer was isolated, dried (MgSO4), and concentrated. The residue was chromatographed on silica gel eluting with ethyl acetate in hexanes (1:1) to give un-reacted 2-bromopyrimidine (130 mg), then the title compound (23 mg). LCMS m/e (288, M+H).

후처리

  1. filtrationfiltered through Celite
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customorganic layer was isolated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with ethyl acetate in hexanes (1:1)
  8. customto give

출처 및 근거

ORD 기록
ord-e45d7b86119f4a91afdadc37a01a965d
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546404B2

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