Ethyl Acetate → HCID 90412743, compound

HRID 1521991Notes

Reaction equation

HRID 1521991 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]2[N:9]([S:25]([C:28]3[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:10]([C:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]=3)=[CH:11][C:3]=12.[F:35][C:36]1[CH:37]=[CH:38][C:39]([O:45][CH3:46])=[C:40](B(O)O)[CH:41]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>CN(C)C=O.O>[Cl:8][C:7]1[C:2]([C:38]2[CH:37]=[C:36]([F:35])[CH:41]=[CH:40][C:39]=2[O:45][CH3:46])=[C:3]2[CH:11]=[C:10]([C:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:14][CH:13]=3)[N:9]([S:25]([C:28]3[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:4]2=[N:5][CH:6]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 67003597HCID 67003597, compound

Product 1

HCID 90412743HCID 90412743, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of Example 229C (0.16 g, 0.306 mmol), (5-fluoro-2-methoxyphenyl)boronic acid (0.062 g, 0.368 mmol) and sodium hydrogencarbonate (0.103 g, 1.225 mmol) in degassed N,N-dimethylformamide (2.55 mL) and water (0.851 mL) was treated with 1,1′-bis(di-t-butylphosphino)ferrocenepalladium dichloride (TCI, 0.014 g, 0.021 mmol) under nitrogen and the mixture was heated at 110° C. for 10 minutes in a Biotage Initiator microwave reactor. Water and ethyl acetate was added and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. Purification by flash chromatography on silica gel (AnaLogix IntelliFlash 280) eluting with a gradient of 0-45% ethyl acetate in heptanes afforded the title compound. MS (ESI+) m/z 612.2 (M+H)+.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (AnaLogix IntelliFlash 280)
  7. washeluting with a gradient of 0-45% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-7e46a3017b8745c6a33f190a0385c477
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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