Potassium Carbonate → HCID 20576922, compound

HRID 1292884Notes

Reaction equation

HRID 1292884 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:15]3=[C:16]([CH2:18][CH2:19][N:14]3[C@@H:13]3[CH2:20][CH2:21][NH:22][CH2:23][C@H:12]23)[CH:17]=1.Cl[CH2:25][CH2:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)=[O:29].C([O-])([O-])=O.[K+].[K+]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:15]3=[C:16]([CH2:18][CH2:19][N:14]3[C@@H:13]3[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][CH2:27][C:28]([C:30]4[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=4)=[O:29])[CH2:23][C@H:12]23)[CH:17]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 20576934HCID 20576934, compound

Product 1

HCID 20576922HCID 20576922, compoundYield 37.2%

Procedure

The title compound (36 mg, 37%) was prepared by the method of Example 189 from (±)-cis-2-(2,4-dichlorophenyl)-4,5,6a,7,8,9,10,10a-octahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole (65.8 mg, 0.19 mmol), 4-chloro-4′-fluorobutyrophenone (50.0 mg, 0.25 mmol), KI (31.5 mg, 0.19 mmol), and K2CO3 (50.0 mg, 0.57 mmol) after chromatographic purification as a white amorphous solid. 1H NMR (CDCl3, 300 MHz) δ 7.90-7.95 (m, 2 H), 7.37 (s, 1H), 7.16 (s, 2H), 7.03 (t, 2H, J=8.8 Hz), 6.91 (s, 1H), 6.85 (s, 1H), 3.49 (bt, 1H, J=8.0 Hz), 3.25-3.45 (m, 2H), 3.02-3.22 (m, 2H), 2.90-3.02 (m, 3H), 2.50-2.88 (m, 2H), 2.10-2.45 (m, 4H), 1.70-2.00 (m, 4H) ppm. MS (CI, NH3): 509 (base, M+H).

Workup

  1. customafter chromatographic purification as a white amorphous solid

Sources & evidence

ORD record
ord-548b89b7f29041e8b766ac4ac456594c
Source dataset
uspto-grants-2007_07
Patent number
US07238690B2

Reaction notes

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