Sodium hydride → HCID 75066246, compound

HRID 2238416Notes

Reaction equation

HRID 2238416 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:6][CH:7]=[C:8]2[C:13]=1[CH:12]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:10]=[CH:9]2.[Cl:26][CH:27]=[CH:28][CH2:29]Cl>CN(C=O)C>[Br:3][C:4]1[C:5]([N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:29][CH:28]=[CH:27][Cl:26])=[CH:6][CH:7]=[C:8]2[C:13]=1[CH:12]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 248831,3-DichloropropeneHCID 44549925HCID 44549925, compound

Product 1

HCID 75066246HCID 75066246, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (57 mg, 1.42 mmol, 60% in oil) was added to a solution of bromide 180 (450 mg, 1.18 mmol) in DMF (5 mL) at 0° C. 1,3-Dichloropropene (260 mg, 2.37 mmol) was added and the mixture was allowed to warm to room temperature over 1 h, then concentrated under reduced pressure CH2Cl2 and water were added and the organic phase was washed with water (×2), brine (×2), dried, and filtered through silica gel to give methyl 8-bromo-7-[(tert-butoxycarbonyl)(3-chloro-2-propen-1-yl)amino]-2-naphthoate (181) (520 mg, 97%) as a yellow oil; 1H NMR (CDCl3) (mixture of rotamers and E and Z forms) δ 9.07 (s, 10H), 8.18-8.08 (m, 1H), 7.93-7.78 (m, 2H), 7.42-7.32 (m, 1H), 6.15-5.98 (m, 2H), 4.01 (s, 3H), 4.63-4.48 (m, 2H), 1.26, 1.24 (2 s, 9H). HRMS (FAB) calcd. for C20H2179Br35ClNO4 (MH+) m/z 454.0421, found 454.0421.

Workup

  1. concentrationconcentrated under reduced pressure CH2Cl2 and water
  2. additionwere added
  3. washthe organic phase was washed with water (×2), brine (×2)
  4. customdried
  5. filtrationfiltered through silica gel

Sources & evidence

ORD record
ord-539a2821c28848cc9f4ca47028471d03
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

Loading…