tert-Butanol → HCID 69418663, compound

HRID 1373549Notes

Reaction equation

HRID 1373549 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2C(O)=O.CC[N:17]([CH2:20]C)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])=CC=1.[CH3:39][C:40]([OH:43])([CH3:42])[CH3:41]>>[C:40]([O:43][C:20](=[O:29])[NH:17][C:7]1[C:8]2[C:3](=[C:2]([Br:1])[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=1)([CH3:42])([CH3:41])[CH3:39]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 6976055-Bromonaphthalene-1-carboxylic acid

Product 1

HCID 69418663HCID 69418663, compoundYield 65%

Procedure

A second intermediate compound, 5-Bromo-naphthalen-1-ylamine, was produced as follows: To a solution of 5-bromo-naphthalene-1-carboxylic acid (10 g, 40 mmol) in t-BuOH (150 mL) was added Et3N (13.6 mL, 80 mmol) and DPPA (10.5 mL, 48 mmol) successively. After the mixture was stirred at room temperature for 1 h, it was refluxed for 16 h. The solvent was then removed and the residue was purified by chromatography on silica gel to give (5-bromo-naphthalen-1-yl)-carbamic acid tert-butyl ester (8.4 g, 65%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.60 (d, J=6.8 Hz, 1H), 8.55 (d, J=6.6 Hz, 1H), 8.50 (d, J=6.2 Hz, 1H), 8.40 (d, J=6.4Hz, 1H), 8.20 (t, J=6.7Hz, 1H), 8.10 (t, J=6.3 Hz, 1H).

Workup

  1. temperatureit was refluxed for 16 h
  2. customThe solvent was then removed
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c69619ac4626422da35a33d7823c42b2
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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