Sodium Carbonate → tert-butyl-N-methyl-N-[1-[[5-(7-methyl-2-pyridin-4-ylimidazo[1,2-a]pyridin-3-yl)-6-[2-tri(propan-2-yl)silylethynyl]pyridin-2-yl]amino]-1-oxopropan-2-yl]-carbamate

HRID 535401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 535401
[CH3:1][N:2]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:3]([CH3:28])[C:4]([NH:6][C:7]1[N:12]=[C:11]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[C:10](B(O)O)=[CH:9][CH:8]=1)=[O:5].I[C:37]1[N:41]2[CH:42]=[CH:43][C:44]([CH3:46])=[CH:45][C:40]2=[N:39][C:38]=1[C:47]1[CH:52]=[CH:51][N:50]=[CH:49][CH:48]=1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>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:32]([O:31][C:29](=[O:30])[N:2]([CH3:1])[CH:3]([CH3:28])[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:37]2[N:41]3[CH:42]=[CH:43][C:44]([CH3:46])=[CH:45][C:40]3=[N:39][C:38]=2[C:47]2[CH:52]=[CH:51][N:50]=[CH:49][CH:48]=2)=[C:11]([C:13]#[C:14][Si:15]([CH:19]([CH3:20])[CH3:21])([CH:22]([CH3:23])[CH3:24])[CH:16]([CH3:18])[CH3:17])[N:12]=1)=[O:5])([CH3:34])([CH3:33])[CH3:35]

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 86694386[6-[2-[Methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoylamino]-2-[2-tri(propan-2-yl)silylethynyl]pyridin-3-yl]boronic acidHCID 866943873-Iodo-7-methyl-2-pyridin-4-ylimidazo[1,2-a]pyridine

Produkt 1

HCID 86694385tert-butyl-N-methyl-N-[1-[[5-(7-methyl-2-pyridin-4-ylimidazo[1,2-a]pyridin-3-yl)-6-[2-tri(propan-2-yl)silylethynyl]pyridin-2-yl]amino]-1-oxopropan-2-yl]-carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of [6-[2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoylamino]-2-[2-tri(propan-2-yl)silylethynyl]pyridin-3-yl]boronic acid D1a (1.5 g, 3.0 mmol), 3-iodo-7-methyl-2-pyridin-4-ylimidazo[1,2-a]pyridine Za (1.3 g, 3.9 mmol), Na2CO3 (0.95 g, 8.9 mmol), Dichlorobis(triphenylphosphine)palladium(II) (209 mg, 0.3 mmol), dioxane (30 ml) and water (5 ml) is stirred under argon atmosphere for 17 h at 70° C. The mixture is diluted with water and extracted with DCM. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 965 mg (49%). HPLC-MS: M+H=667; tR=2.04 min (*Method—3).

Aufarbeitung

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by RP HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2a418d76a6e9410086f144526aeb5c81
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859541B2

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