Triphenylphosphine → 3-(7-bromo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester

HRID 2089471Notes

Reaction equation

HRID 2089471 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH:9]2O)=[CH:4][CH:3]=1.[NH:13]1[CH:17]=[C:16]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[N:15]=[CH:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC)=O)=NC(OC)=O>C1COCC1>[CH:21]([O:20][C:18]([C:16]1[N:15]([CH:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=3)[CH2:6][CH2:7][CH2:8]2)[CH:14]=[N:13][CH:17]=1)=[O:19])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 351621Azodicarboxylic acid dimethyl esterHCID 126949197-Bromo-1,2,3,4-tetrahydronaphthalen-1-olHCID 178459416HCID 178459416, compound

Product 1

HCID 591994563-(7-bromo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 7-bromo-1,2,3,4-tetrahydro-naphthalen-1-ol (2.5 g, 11.0 mmol) and isopropyl 4-imidazolecarboxylate (1.18 g, 7.66 mmol), which can be prepared as described in Example 1, (2.33 g, 10.98 mmol) in THF (20 mL) at 0° C. is added triphenylphosphine and dimethyl azodicarboxylate (40% wt. in toluene, 4.01 g, 10.98 mmol). After 10 min, the cooling bath is removed and after another 30 min, water is added and the mixture is extracted twice with ethyl acetate. The organic layers are dried over magnesium sulfate, filtered, and concentrated. The resulting residue is purified by silica gel chromatography (elution with hexanes-ethyl acetate mixtures) to give 3-(7-bromo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester; MS: (ESI) m/z 363.02, 365.02 (M+H)+; 1H NMR (400 MHz, MeOD) δ ppm 1.42 (d, J=6.1 Hz, 3 H), 1.44 (d, J=6.3 Hz, 3 H), 1.73-1.84 (m, 1 H), 1.89-1.98 (m, 1 H), 2.26-2.40 (m, 2 H), 2.82-2.91 (m, 1 H), 3.00 (dt, J=17.2, 5.6 Hz, 1 H), 5.27-5.37 (m, 1 H), 6.50 (t, J=5.3 Hz, 1 H), 7.26 (d, J=8.3 Hz, 1 H), 7.32 (d, J=2.1 Hz, 1 H), 7.51 (dd, J=8.3, 2.1 Hz, 1 H), 8.23 (d, J=1.5 Hz, 1 H), 8.50 (d, J=1.0 Hz, 1 H).

Workup

  1. customcan be prepared
  2. customthe cooling bath is removed and after another 30 min
  3. additionwater is added
  4. extractionthe mixture is extracted twice with ethyl acetate
  5. dry with materialThe organic layers are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified by silica gel chromatography (elution with hexanes-ethyl acetate mixtures)

Sources & evidence

ORD record
ord-889f6a26606e43ca981a5dcd4273e16b
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

Loading…