Ethyl Acetate → HCID 11238102, compound

HRID 431750Notes

Reaction equation

HRID 431750 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:10][C:9]=1[NH:26][C:27]([C:29]1[NH:30][C:31]2[C:36]([CH:37]=1)=[CH:35][C:34]([O:38][CH3:39])=[C:33]([O:40][CH3:41])[C:32]=2[O:42][CH3:43])=[O:28])(=O)=O.[Li+].[Cl-:45].CCOC(C)=O>CN(C=O)C>[CH2:19]([O:18][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([CH2:7][CH2:6][Cl:45])=[C:9]([NH:26][C:27]([C:29]2[NH:30][C:31]3[C:36]([CH:37]=2)=[CH:35][C:34]([O:38][CH3:39])=[C:33]([O:40][CH3:41])[C:32]=3[O:42][CH3:43])=[O:28])[CH:10]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 433294Lithium ChlorideHCID 11467559HCID 11467559, compound

Product 1

HCID 11238102HCID 11238102, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl methanesulfonate (0.11 g, 0.17 mmol) in dry DMF (2 mL) was added LiCl (0.29 g, 6.94 mmol) at room temperature under N2 atmosphere and stirred for 3 days. The reaction mixture was diluted AcOEt (100 mL) and washed with H2O (20 mL) and saturated aqueous NaCl (10 mL), and then dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica-gel column (AcOEt:Petroleum ether=1:4) to yield as a white solid 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl chloride (75 mg, 81%): mp 180-184° C.; 1H NMR (CDCl3, 500 MHz) δ 9.23 (s, 1H), 8.63 (s, 1H), 8.42 (d, 7.5, 1H), 7.84 (d, 8.5, 1H), 7.53-7.60 (m, 4H), 7.49 (t, 8.0, 1H), 7.44 (t, 7.0, 2H), 7.38 (t, 7.5, 1H), 6.99 (s, 1H), 6.88 (s, 1H), 5.29 (s, 2H), 4.10 (s, 3H), 4.05 (t, 6.0, 2H), 3.96 (s, 3H), 3.93 (s, 3H), 3.60 (t, 6.0, 2H); EIMS m/z 545 (M+); IR (neat) νmax 3271, 2932, 1722, 1634, 1592, 1537, 1503, 1464, 1409, 1370, 1306, 1258, 1237, 1111, 1076, 1050, 998, 910, 830, 761, 736, 700cm−1.

Workup

  1. washwashed with H2O (20 mL) and saturated aqueous NaCl (10 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica-gel column (AcOEt:Petroleum ether=1:4)

Sources & evidence

ORD record
ord-11a30435bd464d08806012bf3f7ed6e6
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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