Triphenylphosphine → HCID 71209455, Verbindung

HRID 1912534

Reaktionsgleichung

[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[C:3]=1[C:18]([O:20][CH3:21])=[O:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:41][C:42]1[CH:47]=[CH:46][C:45]([C@@H:48](O)[CH3:49])=[CH:44][CH:43]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[F:41][C:42]1[CH:47]=[CH:46][C:45]([C@H:48]([N:8]2[C:6]3=[N:7][C:2]([CH3:1])=[C:3]([C:18]([O:20][CH3:21])=[O:19])[C:4]([C:11]4[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=4)=[C:5]3[CH:10]=[CH:9]2)[CH3:49])=[CH:44][CH:43]=1

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

A suspension of methyl 6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (117 mg, 0.417 mmol) (Example 1, Step F) and triphenylphosphine (175 mg, 0.668 mmol) in tetrahydrofuran (THF) (3960 μl) under N2 was treated with (S)-1-(4-fluorophenyl)ethanol (84 μl, 0.668 mmol), heated to 65° C., and treated with DIAD (130 μl, 0.668 mmol). After stirring for 30 min, the reaction was cooled to rt, then concentrated. Purification with column chromatography (0-100% EtOAc/Hexane) afforded (R)-methyl 1-(1-(4-fluorophenyl)ethyl)-6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (18.6 mg, 0.046 mmol, 11.07% yield) as pale yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.37 (d, J=8.1 Hz, 2 H), 7.32-7.18 (m, 4 H), 7.14 (d, J=3.7 Hz, 1 H), 7.03-6.94 (m, 2 H), 6.40-6.28 (m, 2 H), 3.62 (s, 3 H), 2.68 (s, 3 H), 2.41 (s, 3 H), 1.88 (d, J=7.2 Hz, 3 H); LCMS (m/z) ES+=403 (M+1).

Aufarbeitung

temperaturethe reaction was cooled to rt
concentrationconcentrated
customPurification with column chromatography (0-100% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag: ord-0b7c7a3b212948fb84a0fbe1ebee2507
Quelldatensatz: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08609653B2

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