Phosphorus oxychloride → HCID 86614344, compound

HRID 2236109Notes

Reaction equation

HRID 2236109 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.[CH:21]1([CH:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:28](O)=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>ClCCl>[CH:31]1([CH:27]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:28]([N:3]2[CH2:4][CH2:5][C:6]3[N:7]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=4[C:14]=3[CH2:2]2)=[O:29])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

7

Reactant 5

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 97942alpha-Cyclohexylphenylacetic acidHCID 516892Sodium BicarbonateHCID 71552668Ethyl (1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate hydrochloride

Product 1

HCID 86614344HCID 86614344, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step a): To a stirred solution of Intermediate 1 (25 mg, 0.085 mmol), cyclohexyl-phenylacetic acid (27.7 mg, 0.127 mmol) and DIEA (73 μl, 0.424 mmol) in dichloromethane (1 ml) is added POCl3 (9 μl, 0.093 mmol). The resulting yellow reaction mixture is stirred at rt overnight, then saturated aqueous NaHCO3 solution (2 ml) is added. The organic layer is separated and washed with water (2 ml). Evaporation of the solvent gave a crude that is purified by silica gel column chromatography (hexane/EtOAc 3:1) affording ethyl [2-(2-cyclohexyl-2-phenyl-acetyl)-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl]-acetate as a white solid (29 mg) in 74% yield: tR (LC-2) 2.74 min; ESI-MS (positive ion): m/z 459.25 [M+H]+ (calcd 458.59 for C29H34N2O3).

Workup

  1. customThe organic layer is separated
  2. washwashed with water (2 ml)
  3. customEvaporation of the solvent
  4. customgave a crude that
  5. customis purified by silica gel column chromatography (hexane/EtOAc 3:1)

Sources & evidence

ORD record
ord-13b7d5f24e26474dbabe590b61619704
Source dataset
uspto-grants-2010_05
Patent number
US07714132B2

Reaction notes

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