1,2-Dimethoxyethane → 2-Amino-4'-bromo-3'-methoxybiphenyl-4-carbonitrile

HRID 1423352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1423352
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[O:9][CH3:10].[F-].[Cs+].Cl.[NH2:14][C:15]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:16]=1B(O)O.COCCOC>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.O.CCOC(C)=O>[NH2:14][C:15]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:16]=1[C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([O:9][CH3:10])[CH:4]=1

Komponenten

8

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 121872021-Bromo-4-iodo-2-methoxybenzene2×HCID 441187662-Amino-4-cyanobenzeneboronic acid hydrochloride

Produkt 1

HCID 594088822-Amino-4'-bromo-3'-methoxybiphenyl-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of the product from Step 1, -bromo-4-iodo-2-methoxybenzene (750 mg, 2.4 mmol), CsF (1.09 g, 7.2 mmol), (2-amino-4-cyanophenyl)boronic acid hydrochloride (390 mg, 2.4 mmol), and Pd(PPh3)4 (277 mg, 0.24 mmol) was added DME (15 mL) under N2. It was then heated to 100° C. After 36 h, to the thick red suspension was added EtOAc and water. The organic layer was washed with brine, dried over Na2SO4, and the solvent was removed in vacuo. The residue was purified on silica (gradient elution, 3-50% EtOAc/hex) to yield the title compound as a red oil. LRMS (M+H)+=303.1.

Aufarbeitung

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified on silica (gradient elution, 3-50% EtOAc/hex)

Quellen und Nachweise

ORD-Eintrag
ord-5d5018787fad4706b2820eaac318c9dc
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927569B2

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