Potassium Carbonate → HCID 86590134、化合物

HRID 1840521ノート

反応式

HRID 1840521 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][C:12]([CH3:26])([O:14][C:15]([NH:17][C@@H:18]([CH2:23][C:24]#[CH:25])[C:19]([O:21][CH3:22])=[O:20])=[O:16])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.[Cu](I)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>[CH3:13][C:12]([CH3:26])([O:14][C:15]([NH:17][C@@H:18]([CH2:23][C:24]#[C:25][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[C:19]([O:21][CH3:22])=[O:20])=[O:16])[CH3:11]

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 782402-Bromo-5-nitropyridineHCID 11817013(S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoate

生成物 1

HCID 86590134HCID 86590134、化合物収率 65%

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A mixture of 2-bromo-5-nitropyridine (10.0 g; 49.0 mmol), methyl (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]pent-4-ynoate (13.34 g; 58.8 mmol), copper iodide (0.465 g; 2.5 mmol), potassium carbonate (13.6 g; 98.0 mmol) and dichlorobis(triphenylphosphine)palladium (1.7 g; 2.5 mmol) in 30 ml of anhydrous dimethylformamide (DMF) is heated for 4 hours at 60° C. under argon. The reaction mixture is taken up in 800 ml of ethyl acetate, washed with 2×400 ml of water, 400 ml of saturated hydrogen carbonate and 400 ml of brine, dried over sodium sulphate, filtered and then concentrated under reduced pressure. The residue obtained is purified on a column of silica, eluting with a cyclohexane/ethyl acetate gradient of from 0 to 20% ethyl acetate. 11 g of methyl (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(5-nitropyrid-2-yl)pent-4-ynoate is isolated.

後処理

  1. washwashed with 2×400 ml of water, 400 ml of saturated hydrogen carbonate and 400 ml of brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customis purified on a column of silica
  7. washeluting with a cyclohexane/ethyl acetate gradient of from 0 to 20% ethyl acetate

出典と根拠

ORDレコード
ord-faa9066029644151b344ebe3cf4afd74
出典データセット
uspto-grants-2004_01
特許番号
US06680329B2

反応ノート

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