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

HRID 1244124노트

반응식

HRID 1244124 반응식
Br[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.[CH2:21]([OH:25])[CH2:22][C:23]#[CH:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(NCC)C>CN(C=O)C.[Cu]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>[OH:17][C:15]1[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:24]#[C:23][CH2:22][CH2:21][OH:25])=[CH:3][CH:4]=3)=[CH:9][S:10][C:11]=2[NH:12][C:13](=[O:20])[C:14]=1[C:18]#[N:19]

참가 물질

8

반응물 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 135663-Butyn-1-OLHCID 546964233-(4-Bromophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

생성물 1

HCID 546898814-Hydroxy-3-[4-(4-hydroxybut-1-ynyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

To an ambient slurry of 3-(4-bromophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (0.050 g, 0.14 mmol), but-3-yn-1-ol (0.030 g, 0.42 mmol), copper(I) iodide (0.005 g), triphenylphosphine (0.009 g, 0.03 mmol) and diethyl amine (0.15 mL, 1.4 mmol) in DMF (1.5 mL) was added dichlorobis(triphenylphosphine)palladium(II) (0.002 g, 0.003 mmol) in a single portion. The reaction was heated at 120° C. for 20 min in a microwave, cooled to room temperature, filtered, concentrated and purified by RP-HPLC to afford the title compound. MS (ESI) m/e 334.9 (M−H)+; 1H NMR (300 MHz, DMSO-d6): δ ppm 12.02 (br s, 1H), 7.39 (d, J=9, 2H), 7.35 (d, J=9, 2H), 6.94 (s, 1H), 3.59 (t, J=9, 2H), 2.57 (t, J=9, 2H).

후처리

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompurified by RP-HPLC

출처 및 근거

ORD 기록
ord-e9d235bf69144817a3e6ee1151597227
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119205B2

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