Sodium Hydroxide → HCID 178480264, compound

HRID 2064495Notes

Reaction equation

HRID 2064495 reaction equation
[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][CH:12]2[CH2:14][CH2:13]2)[C:7](=[NH:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[Br:18][C:19]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:20]=1[C:21](Cl)=[O:22]>O1CCCC1.O.C(OCC)(=O)C>[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][CH:12]2[CH2:13][CH2:14]2)/[C:7](=[N:15]/[C:21](=[O:22])[C:20]2[CH:24]=[C:25]([C:28]([F:29])([F:30])[F:31])[CH:26]=[CH:27][C:19]=2[Br:18])/[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 59865659HCID 59865659, compoundHCID 790215092-Bromo-5-(trifluoromethyl)benzoyl chloride

Product 1

HCID 178480264HCID 178480264, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 3E (3.52 g, 17 mmol) in tetrahydrofuran (20 mL) was added sodium hydroxide (2.72 g, 68 mmol) in water (5.00 mL), followed by addition of a solution of 2-bromo-5-(trifluoromethyl)benzoyl chloride (3.85 g, 17 mmol) in tetrahydrofuran (5 mL) dropwise at 0° C. The mixture was stirred at room temperature for 1 hour then diluted with water (20 mL) and ethyl acetate (30 mL). The layers were separated and the organic extract was washed with brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, eluted with a gradient of 15-100% hexane in solvent B, solvent B: 10:1:0.5 ethyl acetate:methanol:triethylamine) to afford the title compound (6.3 g, 93%). 1H NMR (300 MHz, DMSO-D6) δ ppm 0.41-0.52 (m, 4H) 1.13-1.27 (m, 1H) 1.40 (s, 9H) 3.94 (s, 3H) 4.20 (d, J=6.74 Hz, 2H) 6.83 (s, 1H) 7.54 (dd, J=8.53, 2.18 Hz, 1H) 7.77-7.82 (m, 2H); MS (ESI) m/z 458 [M+H]+.

Workup

  1. customThe layers were separated
  2. extractionthe organic extract
  3. washwas washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography
  8. washeluted with a gradient of 15-100% hexane in solvent B, solvent B

Sources & evidence

ORD record
ord-c44fba441eb1495e93fa8de96eafeb4c
Source dataset
uspto-grants-2012_10
Patent number
US08288428B2

Reaction notes

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