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Diethylamine → 3-[4-(5-Cyanopent-1-ynyl)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

HRID 1244140
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HRID 1244140 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([OH:17])=[C:14]([C:18]#[N:19])[C:13](=[O:20])[NH:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.C(NCC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:45](#[N:51])[CH2:46][CH2:47][CH2:48][C:49]#[CH:50]>CN(C=O)C.[Cu]I>[C:45]([CH2:46][CH2:47][CH2:48][C:49]#[C:50][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([OH:17])=[C:14]([C:18]#[N:19])[C:13](=[O:20])[NH:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1)#[N:51]
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참가 물질

7

반응물 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 1398525-HexynenitrileHCID 546899454-Hydroxy-3-(4-iodophenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

생성물 1

HCID 546899353-[4-(5-Cyanopent-1-ynyl)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

시약·촉매·용매 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-(4-iodo-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (60 mg, 0.15 mmol) in 1.5 mL DMF was added diethylamine (0.16 mL, 1.5 mmol), followed by copper(I) iodide (trace), Pd(PPh3)Cl2 (3.5 mg, 0.005 mmol), and triphenylphosphine (12 mg, 0.04 mmol). The resulting mixture was stirred at rt for 5 min, after which hex-5-ynenitrile (50 μL, 0.5 mmol) was added. The reaction was then heated to 90° C. using microwave reactor for 20 min, filtered, concentrated and purified by reverse phase HPLC to give the titled compound. MS (ESI) m/e 358 (M−H)+; 1H NMR (300 MHz, DMSO-d6): δ 1.82–1.91 (m, 2H), 2.56 (t, J=7.12 Hz, 2H), 2.65 (t, J=7.12 Hz, 2H), 6.67 (s, 1H), 7.31 (d, J=8.48 Hz, 2H) 7.43 (d, J=8.48, 2H), 10.80 (s, 1H).

후처리

  1. temperatureThe reaction was then heated to 90° C.
  2. customfor 20 min
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-d9da70857e1e4ce5a461533f12463de1
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07119205B2

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