Ethyl chloroformate → (+/-)-tert-Butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-2-ethoxy-2-oxoethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174105
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH2:11][C:12]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH3:23])=[C:17]4[C:13]=3[CH:14]=[CH:15][N:16]4[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:8][C:7]=2[CH:31]=1)#[N:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl[C:43]([O:45][CH2:46][CH3:47])=[O:44]>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([C:12]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH3:23])=[C:17]4[C:13]=3[CH:14]=[CH:15][N:16]4[C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[C:43]([O:45][CH2:46][CH3:47])=[O:44])=[N:8][C:7]=2[CH:31]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 10928Ethyl chloroformateHCID 2733832Lithium HexamethyldisilazideHCID 86701743tert-Butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Produkt 1

HCID 86701744(+/-)-tert-Butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-2-ethoxy-2-oxoethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of tert-butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 144-A) (60 mg, 0.144 mmol) in THF (2.1 mL) under nitrogen at −78° C. was added LiHMDS (0.359 ml, 0.359 mmol) in THF. After 10 mins, ethyl chloroformate (0.276 mL, 2.87 mmol) was added and the reaction was warmed to room temperature. After 5 mins the reaction was quenched with sat. aq. NH4Cl, the layers were separated and the aqueous layer extracted with EtOAc. The EtOAc layer was concentrated, purified via FCC with Hep/EtOAc to obtain the title compound. MS (ESI+) m/z 490.0 (M+H).

Aufarbeitung

  1. customAfter 5 mins the reaction was quenched with sat. aq. NH4Cl
  2. customthe layers were separated
  3. extractionthe aqueous layer extracted with EtOAc
  4. concentrationThe EtOAc layer was concentrated
  5. custompurified via FCC with Hep/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-c9453a66eac6486cb507ab229788f510
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056874B2

Notizen zur Reaktion

Wird geladen…