18-Crown-6 → HCID 54339822, compound

HRID 1387415Notes

Reaction equation

HRID 1387415 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Br:21])[C:19]=1[OH:20])[CH:5]=[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:15])[CH:13]=2)[NH:8][C:7]1=[O:16].[CH3:22]C(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.ClC[CH2:48][C:49]([CH3:54])([CH3:53])[C:50]([O-:52])=[O:51]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Br:21])[C:19]=1[O:20][CH2:22][O:52][C:50](=[O:51])[C:49]([CH3:54])([CH3:53])[CH3:48])[CH:5]=[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:15])[CH:13]=2)[NH:8][C:7]1=[O:16]

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 217530474-Chloro-2,2-dimethylbutanoateHCID 23665647Potassium tert-butoxideHCID 54084320HCID 54084320, compound

Product 1

HCID 54339822HCID 54339822, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(3,5-dibromo-4-hydroxy-benzylidene)-2-oxo-2,3-dihydro-5-chloro-1 H-indole (0.43 g, 1.0 mmol) in dry acetonitrile (20 mL) under nitrogen was treated with potassium tert-butoxide (0.12 g, 1.1 mmol) at room temperature. The resulting orange heterogenous mixture was treated with 18-crown-6 (0.053 g, 0.20 mmol) and stirred for 15 minutes before adding chloromethylpivalate (0.40 mL, 2.8 mmol). The reaction was heated to seventy degrees celsius, stirred for three hours then filtered while hot. The filtrate was allowed to cool to room temperature and stirred overnight. The resulting solids were collected on a filter, washed with acetonitrile and dried under vacuum to provide the title compound (0.24 g, 44%) as a mixture of E/Z isomers. 1H NMR (DMSO-d6): (mixture of E/Z isomers) δ10.93 (s, 1H), 10.87(s, 1H), 8.85 (s, 2H), 8.09 (s, 2H), 7.94 (s, 1H), 7.84 (d, 1H), 7.67 (s, 1H), 7.32-7.39 (m, 3H), 6.96 (d, 1H), 6.91 (d, 1H), 5.91 (s, 2H), 5.88 (s, 2H), 1.23 (s, 9H), 1.22 (s, 9H). MS (ES-): 542 (60) (M−1). Anal. Calcd for C21H18NO4ClBr2: C, 46.40; H, 3.34; N, 2.58. Found: C, 46.33; H, 3.30; N, 2.55.

Workup

  1. temperatureThe reaction was heated to seventy degrees celsius
  2. stirringstirred for three hours
  3. filtrationthen filtered while hot
  4. stirringstirred overnight
  5. customThe resulting solids were collected on a filter
  6. washwashed with acetonitrile
  7. customdried under vacuum

Sources & evidence

ORD record
ord-44f02ba9ab86406cafa5989dfbbdd588
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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