Triethylamine → Tert-butyl{3-[(2-methoxy-5-nitrophenyl)ethynyl]phenyl}carbamate

HRID 541572

Reaktionsgleichung

Reaktionsgleichung von HRID 541572
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1)#[CH:2].I[C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=1[O:27][CH3:28].C(N(CC)CC)C>CN(C)C=O.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>[C:12]([O:11][C:10](=[O:16])[NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[C:2][C:20]2[CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[CH:23]=[CH:18][C:19]=2[O:27][CH3:28])[CH:4]=1)([CH3:13])([CH3:15])[CH3:14]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 948062-Iodo-1-methoxy-4-nitrobenzeneHCID 11275982tert-Butyl 3-ethynylphenylcarbamate

Produkt 1

HCID 57961666Tert-butyl{3-[(2-methoxy-5-nitrophenyl)ethynyl]phenyl}carbamateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

tert-Butyl (3-ethynylphenyl)carbamate was stirred with 2-iodo-1-methoxy-4-nitrobenzene (2.60 g, 9.31 mmol) and bis(triphenylphosphine)palladium(II) chloride (163 mg, 0.23 mmol) in N,N-dimethylformamide (15 mL), and triethylamine (2.59 mL, 18.6 mmol) was added. The reaction mixture was heated at 80° C. for 15 minutes. Purification by preparative LCMS (pH 10) gave the desired compound (1.38 g, 40%). 1H NMR (300 MHz, DMSO-d6): δ 9.53 (s, 1H), 8.25 (m, 2H), 7.71 (s, 1H), 7.42 (d, 1H), 7.25 (m, 2H), 7.18 (d, 1H), 4.00 (s, 3H), 1.42 (s, 9H). LCMS for C20H21N2O5 (M+H)+: m/z=369.1.

Aufarbeitung

  1. additionwas added
  2. customPurification by preparative LCMS (pH 10)

Quellen und Nachweise

ORD-Eintrag
ord-974a337b796049089504cf9eeee21670
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871753B2

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