Sodium hydride → 188533-07-5

HRID 716088Notes

Reaction equation

HRID 716088 reaction equation
[H-].[Na+].[Br:3][CH:4]([CH2:16][CH2:17]Br)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:6]>C1COCC1>[Br:3][CH:4]1[CH2:16][CH2:17][N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:5]1=[O:6]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 18978618HCID 18978618, compound2×

Product 1

HCID 18978811188533-07-5Yield 76.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 60% dispersion of NaH in mineral oil (1.70 g, 42.5 mmol) was added to a stirred solution of 2,4-dibromo-N-(4-fluorobenzyl)butanamide (10.0 g, 28.3 mmol, intermediate Q) in THF (25 mL) at 0° C. The reaction mixture was allowed to warm to rt and stir for and additional 2 h. The reaction mixture was carefully quenched with ice and diluted with water. The resulting mixture was extracted with EtOAc. The combined organic layers were washed with water and then brine solution. The organic layer was over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified using silica gel column chromatography (10% EtOAc/hexanes) to afford the desired product (5.90 g, 64% yield): LCMS (ES-API), m/z 272.4, 274.3 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.12-2.27 (m, 1H) 2.56-2.68 (m, 1H) 3.27 (dd, J=7.78, 3.26 Hz, 2H) 4.29-4.38 (m, 1H) 4.40-4.57 (m, 1H) 4.73 (dd, J=7.03, 3.01 Hz, 1H) 7.04-7.35 (m, 4H).

Workup

  1. customThe reaction mixture was carefully quenched with ice
  2. additiondiluted with water
  3. extractionThe resulting mixture was extracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-d684da7b586c4c879f20416ea6933723
Source dataset
uspto-grants-2015_11
Patent number
US09187506B2

Reaction notes

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