1-Naphthalenecarbonyl chloride → HCID 71552330, compound

HRID 2236106Notes

Reaction equation

HRID 2236106 reaction equation
Cl.[CH2:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=2[CH2:5][CH2:4][NH:3]1.CCN(C(C)C)C(C)C.[C:30]1([C:40](Cl)=[O:41])[C:39]2[C:34](=CC=CC=2)[CH:33]=[CH:32][CH:31]=1>ClCCl>[C:40]([N:3]1[CH2:4][CH2:5][C:6]2[N:7]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]=2[CH2:2]1)(=[O:41])[C:30]1[CH:39]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 701461-Naphthalenecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 71552668Ethyl (1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate hydrochloride

Product 1

HCID 71552330HCID 71552330, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step a): To a stirred solution of Intermediate 1 (ethyl (1,2,3,4-tetrahydro-pyrido[4,3b]indol-5-yl)-acetate hydrochloride, 25.0 mg, 0.085 mmol) and DIEA (73 μl, 0.425 mmol) in dichloromethane (0.5 ml) is added naphthoyl chloride (15 mg, 0.11 mmol). The resulting yellow solution was kept stirring at rt for 1 h and then is quenched by adding saturated aqueous NaHCO3 solution (2 ml). The organic layer is separated and washed with water (2 ml). After removal of the solvent, crude ethyl (2-benzoyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate is obtained pure as a yellow glassy solid: tR (LC-2) 2.20 min; ESI-MS (positive ion): m/z 386.31 [M+Na]+ (calcd 362.42 for C22H22N2O3).

Workup

  1. customis quenched
  2. additionby adding saturated aqueous NaHCO3 solution (2 ml)
  3. customThe organic layer is separated
  4. washwashed with water (2 ml)
  5. customAfter removal of the solvent

Sources & evidence

ORD record
ord-163b1868f2ab4167891aa1ba24cd561f
Source dataset
uspto-grants-2010_05
Patent number
US07714132B2

Reaction notes

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