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

HRID 1038043
ノート
印刷プレビュー

反応式

HRID 1038043 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 783452-Bromopyrimidine2 回HCID 15550481tert-Butyl 4-ethynylpiperidine-1-carboxylate

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476
HCID 178418476、化合物
触媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e45d7b86119f4a91afdadc37a01a965d
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546404B2

反応ノート

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