Potassium Carbonate → HCID 44549924, compound

HRID 2238411Notes

Reaction equation

HRID 2238411 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C1C(=O)N([Br:29])C(=O)C1.C([O-])([O-])=O.[K+].[K+]>CC#N>[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:11]2[Br:29])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 44549669HCID 44549669, compound

Product 1

HCID 44549924HCID 44549924, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of carbamate 170 (420 mg, 1.47 mmol), NBS (292 mg, 1.62 mmol) and K2CO3 (244 mg, 1.77 mmol) in MeCN (10 mL) was heated at 40° C. under N2 for 30 min then concentrated under reduced pressure. EtOAc and water were added to the residue, and the EtOAc portion was washed with water, brine and dried to give tert-butyl 7-acetyl-1-bromo-2-naphthylcarbamate (171) (530 mg, 99%) as a colorless solid: mp (petroleum ether/EtOAc) 114-117° C.; 1H NMR (CDCl3) δ 8.70 (s, 1H), 8.50 (d, J=9.0 Hz, 1H), 7.97 (dd, J=3.5, 1.6 Hz, 1H), 7.84 (d, J=8.8 Hz, 1H), 7.81 (d, J=9.6 Hz, 1H), 7.34 (br s, 1H), 2.76 (s, 3H), 1.58 (s, 9H); 13C NMR δ 197.9, 152.4, 136.0, 135.8, 133.0, 131.5, 128.7, 128.5, 128.0, 123.1, 122.0, 111.0, 81.6, 28.3, 26.7. Anal. (C17H18BrNO3) C, H, N.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. additionEtOAc and water were added to the residue
  3. washthe EtOAc portion was washed with water, brine
  4. customdried

Sources & evidence

ORD record
ord-6f0a99646ba141a7ab53de985ded414c
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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