Potassium Carbonate → HCID 58677614, compound

HRID 1012662Notes

Reaction equation

HRID 1012662 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH:5]=[CH:4][C:3]=1[C:18]([C:20]1[CH:25]=[C:24]([OH:26])[CH:23]=[CH:22][C:21]=1[F:27])=[O:19].Cl.Cl[CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH:5]=[CH:4][C:3]=1[C:18]([C:20]1[CH:25]=[C:24]([O:26][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:23]=[CH:22][C:21]=1[F:27])=[O:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 67315029[2-Chloro-4-(2-nitro-phenylamino)-phenyl]-(2-fluoro-5-hydroxy-phenyl)-methanone

Product 1

HCID 58677614HCID 58677614, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

Compound 517 (30 mg, 0.08 mmol) was dissolved in acetonitrile (2 mL) in a reaction vial. 4-(2-Chloro-ethyl)-morpholine hydrochloride (44 mg, 0.24 mmol) and K2CO3 (33 mg, 0.24 mmol) were added. The reaction vial was flushed with argon, closed and then stirred at 130° C. for a total of 105 min. in a microwave oven. The reaction mixture was poured into a mixture of EtOAc:H2O (1:1, 10 mL). The layers were separated and the aqueous phase was extracted with EtOAc (2×10 mL). The combined organic layers were dried (MgSO4), filtered, concentrated in vacuo and purified by continuously gradient flash chromatography using EtOAc/petroleum ether (40-60)(v:v=1:9 to 3:2) as the eluent, affording the title compound as a light yellow oil.

Workup

  1. customThe reaction
  2. customvial was flushed with argon
  3. customclosed
  4. additionThe reaction mixture was poured into a mixture of EtOAc:H2O (1:1, 10 mL)
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with EtOAc (2×10 mL)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. custompurified by continuously gradient flash chromatography

Sources & evidence

ORD record
ord-085f2a02870e495ea6b2fafc222a3edf
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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