Potassium Carbonate → 1-Methylethyl {(cis)-1-acetyl-2-methyl-6-[5-(1-piperidinylmethyl)-2-pyridinyl]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

HRID 2366926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366926
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][N:3]=1.[CH3:15][CH:16]([O:18][C:19](=[O:44])[NH:20][C@H:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28](B3OC(C)(C)C(C)(C)O3)[CH:29]=2)[N:24]([C:40](=[O:42])[CH3:41])[C@@H:23]([CH3:43])[CH2:22]1)[CH3:17].CC(OC(=O)NC1C2C(=CC=C(B3OC(C)(C)C(C)(C)O3)C=2)N(C(=O)C)C(C)C1)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[C:40]([N:24]1[C:25]2[C:30](=[CH:29][C:28]([C:2]3[CH:7]=[CH:6][C:5]([CH2:8][N:9]4[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]4)=[CH:4][N:3]=3)=[CH:27][CH:26]=2)[C@H:21]([NH:20][C:19](=[O:44])[O:18][CH:16]([CH3:15])[CH3:17])[CH2:22][C@@H:23]1[CH3:43])(=[O:42])[CH3:41]

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 234379942-Bromo-5-(piperidin-1-ylmethyl)pyridineHCID 681853941-Methylethyl [(cis)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamateHCID 774200021-Methylethyl [1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate

Produkt 1

HCID 866692711-Methylethyl {(cis)-1-acetyl-2-methyl-6-[5-(1-piperidinylmethyl)-2-pyridinyl]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

2-bromo-5-(1-piperidinylmethyl)pyridine (for a preparation see Intermediate 24) (98 mg, 0.384 mmol) was mixed with 1-methylethyl[(cis)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 12) (100 mg, 0.240 mmol), potassium carbonate (66.4 mg, 0.480 mmol) and tetrakis(triphenylphosphine)palladium(0) (13.88 mg, 0.012 mmol), dissolved in ethanol (1 mL) and toluene (1 mL) and stirred under nitrogen at 90° C. The reaction mixture was loaded onto a 5 g SCX column, eluting with MeOH (30 mL) followed by 2M MeOH/NH3 (30 mL). Product-containing fractions were evaporated to dryness to give a yellow solid (155 mg). This was purified by MDAP. Product-containing fractions were evaporated to dryness to give a clear, colourless solid (55 mg). LCMS (Method C): Rt=0.67, MH+=465

Aufarbeitung

  1. washeluting with MeOH (30 mL)
  2. customProduct-containing fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-bcd2c89b2f3443f2bb50cdccb225dd91
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697725B2

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