Triethylamine → 2-{[2-(hex-1-yn-1-yl)-1,3-thiazol-4-yl]methoxy}-1H-isoindole-1,3(2H)-dione

HRID 2039682

반응식

HRID 2039682 반응식
Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[N:6]=1.[CH:20]#[C:21][CH2:22][CH2:23][CH2:24][CH3:25].C(N(CC)CC)C>O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].[Cu](I)I>[C:20]([C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[N:6]=1)#[C:21][CH2:22][CH2:23][CH2:24][CH3:25]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 127321-HexyneHCID 674242932-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 674260462-{[2-(hex-1-yn-1-yl)-1,3-thiazol-4-yl]methoxy}-1H-isoindole-1,3(2H)-dione수율 59%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione (23.1 g, 68.1 mmol) in dry tetrahydrofuran (300 mL) were added 1-hexyne (11.2 g, 136 mmol), triethylamine (13.8 g, 136 mmol). The reaction mixture was degassed by blowing a flow of Argon through it, then palladium tetrakis(triphenylphosphine) (3.94 g, 3.41 mmol) and copper iodide (1.30 g, 6.81 mmol) were added. After stirring at room temperature for 21 h under argon, the mixture was concentrated in vacuo, diluted with water (800 mL) and ethyl acetate (900 mL), the organic layer was washed with water, dried (MgSO4) and concentrated in vacuo. Purification on silica gel afforded 2-{[2-(hex-1-yn-1-yl)-1,3-thiazol-4-yl]methoxy}-1H-isoindole-1,3(2H)-dione [13.6 g, yield 59%; HPLC/MS: m/z=341 (M+H); log P(HCOOH)=3.78].

후처리

  1. customThe reaction mixture was degassed
  2. concentrationthe mixture was concentrated in vacuo
  3. additiondiluted with water (800 mL) and ethyl acetate (900 mL)
  4. washthe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification on silica gel

출처 및 근거

ORD 기록
ord-a5fec88c4a134e67ba5d586535e0548f
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580799B2

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