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Diisopropylethylamine → 5-(3-Fluoro-phenylethynyl)-pyridine-2-carboxylic acid tert-butyl-ethyl-amide

HRID 2199412
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HRID 2199412 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]([OH:18])=O)=[N:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:28]([NH:32][CH2:33][CH3:34])([CH3:31])([CH3:30])[CH3:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>O1CCOCC1>[C:28]([N:32]([CH2:33][CH3:34])[C:16]([C:13]1[CH:12]=[CH:11][C:10]([C:9]#[C:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[CH:15][N:14]=1)=[O:18])([CH3:31])([CH3:30])[CH3:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 521156N-tert-ButylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 533848625-((3-Fluorophenyl)ethynyl)picolinic acid

생성물 1

HCID 736028105-(3-Fluoro-phenylethynyl)-pyridine-2-carboxylic acid tert-butyl-ethyl-amide수율 76.7%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

(100 mg, 0.41 mmol) 5-(3-Fluoro-phenylethynyl)-pyridine-2-carboxylic acid (Example 1, step 2) was dissolved in dioxane (1 ml) and Hunig's Base (217 μl, 1.24 mmol, 3 equiv.), tert.-butylethylamine (63 mg, 0.62 mmol, 1.5 equiv.) and TBTU (146 mg, 0.45 mmol, 1.1 equiv.) were added at room temperature. The mixture was stirred for 16 hours at room temperature. The reaction mixture was evaporated and extracted saturated NaHCO3 solution and two times with a small volume of dichloromethane. The crude product was purified by flash chromatography by directly loading the dichloromethane layers onto a silica gel column and eluting with an ethyl acetate:heptane gradient 0:100 to 0:100. The desired 5-(3-fluoro-phenylethynyl)-pyridine-2-carboxylic acid tert-butyl-ethyl-amide (102 mg, 76% yield) was obtained as a light yellow oil, MS: m/e=325.3 (M+H+).

후처리

  1. customThe reaction mixture was evaporated
  2. extractionextracted saturated NaHCO3 solution and two times with a small volume of dichloromethane
  3. customThe crude product was purified by flash chromatography
  4. washeluting with an ethyl acetate

출처 및 근거

ORD 기록
ord-61549898245a41be9e6498ba466a0377
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09359301B2

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