N-bromobutanimide → tert-Butyl (6-amino-5-bromonaphthalen-2-yl)carbamate

HRID 64512Notes

Reaction equation

HRID 64512 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=[CH:5]2.C([O-])(=O)C.[NH4+].[Br:25]N1C(=O)CCC1=O>CC#N>[NH2:1][C:2]1[C:3]([Br:25])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 517165Ammonium AcetateHCID 117604992N2-Boc-naphthalene-2,6-diamine

Product 1

HCID 131737224tert-Butyl (6-amino-5-bromonaphthalen-2-yl)carbamateYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

tert-Butyl (6-aminonaphthalen-2-yl)carbamate (1.31 g, 5.07 mmol) was stirred with ammonium acetate (39 mg, 0.5 mmol) in MeCN in an ice bath. N-Bromosuccinimide (948 mg, 5.32 mmol) was dissolved in additional MeCN and added slowly over 1 h. Stirring was continued for 1 h at 0° C., and then Celite was added. Solvents were removed under reduced pressure, and the product (1.33 g, 78%) isolated by silica gel chromatography eluting with a gradient of 0→50% EtOAc in heptanes. 1H NMR (CD2Cl2) d 7.94 (d, 1H); 7.89 (br d, 1H); 7.58 (d, 1H); 7.38 (dd, 1H); 7.02 (d, 1H); 6.66 (br s, 1H); 4.35 (br s, 2H); 1.54 (s, 9H).

Workup

  1. additionadded slowly over 1 h
  2. additionCelite was added
  3. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-e195f64c2b934f7eba13c9d385a3b3fb
Source dataset
uspto-grants-2016_09
Patent number
US09447450B2

Reaction notes

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