Potassium Carbonate → HCID 20576923, compound

HRID 1266071Notes

Reaction equation

HRID 1266071 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]2[C:14]3=[C:15]([CH2:17][CH2:18][N:13]3[C@@H:12]3[CH2:19][CH2:20][NH:21][CH2:22][C@H:11]23)[CH:16]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:30][CH2:31][CH2:32][C:33]([C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1)=[O:34]>CCC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]2[C:14]3=[C:15]([CH2:17][CH2:18][N:13]3[C@@H:12]3[CH2:19][CH2:20][N:21]([CH2:30][CH2:31][CH2:32][C:33]([C:35]4[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=4)=[O:34])[CH2:22][C@H:11]23)[CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 20576952HCID 20576952, compound

Product 1

HCID 20576923HCID 20576923, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

(±)-Cis-2-(2-chlorophenyl)-4,5,6a,7,8,9,10,10a-octahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole (26.4 mg, 0.085 mmol) 0.7 ml of MEK. KI (14 mg, 0.085 mmol) and K2CO3 (22 mg, 0.26 mmol), and 4-chloro-4′-fluorobutyrophenone (22.2 mg, 0.11 mmol) were added. The suspension was refluxed for 48 h and then cooled to rt. The suspension was filtered and the residue was washed with CH2Cl2 (5 ml). The solution was concentrated in vacuo. The residue was purified by column chromatography (10% MeOH—CH2Cl2) to afford the title compound (18.8 mg, 47%) as a white amorphous solid. 1H NMR (CDCl3, 300 MHz) δ8.00-8.04 (m, 2 H), 7.41 (dd, 1H, J=1.5, 7.3 Hz), 7.30 (dd, 1H, J=1.8, 7.3 Hz), 7.10-7.20 (m, 4H), 7.01 (s, 1H), 6.96 (s, 1H), 3.68 (bt, 1H, J=6.6 Hz), 3.30-3.50 (m, 2H), 3.10-3.30 (m, 2H), 2.92-3.08 (m, 3H), 2.60-2.92 (m, 2H), 2.38-2.58 (m, 3H), 2.27 (t, 1H, J=11.3 Hz), 1.70-2.05 (m, 4H) ppm. MS (CI, NH3): 475 (base, M+H).

Workup

  1. temperatureThe suspension was refluxed for 48 h
  2. filtrationThe suspension was filtered
  3. washthe residue was washed with CH2Cl2 (5 ml)
  4. concentrationThe solution was concentrated in vacuo
  5. customThe residue was purified by column chromatography (10% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-b5bde2a87e43484b9b965f0b62993f1a
Source dataset
uspto-grants-2003_04
Patent number
US06548493B1

Reaction notes

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