Potassium Carbonate → HCID 44549925, compound

HRID 2238415Notes

Reaction equation

HRID 2238415 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:16]2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:30])C(=O)C1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:30][C:18]1[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:10][CH:11]=[C:12]2[C:17]=1[CH:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:14]=[CH:13]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 44549670HCID 44549670, compound

Product 1

HCID 44549925HCID 44549925, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 179 (50 mg, 0.17 mmol), NBS (33 mg, 0.18 mmol) and K2CO3 (28 mg, 0.20 mmol) in MeCN (3 mL) was heated at 60° C. under N2 for 30 min. The solvent was removed under reduced pressure and the residue was purified by chromatography eluting with petroleum ether/EtOAc (9:1) followed by recrystallization (petroleum ether) to give methyl 8-bromo-7-[(tert-butoxycarbonyl)amino]-2-naphthoate (180) (57 mg, 90%) as colorless crystals: mp 137-140° C.; 1H NMR (CDCl3) δ 8.89 (d, J=1.2 Hz, 1H), 8.49 (d, J=9.1 Hz, 1H), 8.01 (dd, J=8.6, 1.7 Hz, 1H), 7.83 (d, J=8.6 Hz, 1H), 7.82 (d, J=9.0 Hz, 1H), 7.35 (br s, 1H), 4.00 (s, 3H), 1.57 (s, 9H). Anal. (C17H18BrNO4) C, H, N, Br.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by chromatography
  3. washeluting with petroleum ether/EtOAc (9:1)
  4. customfollowed by recrystallization (petroleum ether)

Sources & evidence

ORD record
ord-71dda36466044dfaab77a987627dddd3
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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