Potassium Carbonate → HCID 10177555, compound

HRID 1793565Notes

Reaction equation

HRID 1793565 reaction equation
[CH:1]1[C:10]2[C:11]3[CH2:16][N:15]=[CH:14][CH2:13][C:12]=3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][CH:2]=1.Cl[CH2:18][CH2:19][CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=[O:22].C([O-])([O-])=O.[K+].[K+]>>[F:29][C:26]1[CH:25]=[CH:24][C:23]([C:21](=[O:22])[CH2:20][CH2:19][CH2:18][N:15]2[CH2:14][CH2:13][C:12]3[N:8]4[C:9]5[C:4](=[CH:3][CH:2]=[CH:1][C:10]=5[C:11]=3[CH2:16]2)[CH2:5][CH2:6][CH2:7]4)=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 22021694HCID 22021694, compound

Product 1

HCID 10177555HCID 10177555, compoundYield 28%

Procedure

The title compound (0.060 g, 28%) was prepared by the general method of Example 402 from 5,6,8,11-tetrahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (0.12 g, 0.57 mmol), 4-chloro-4′-fluorobutyrophenone (0.40 g, 2.0 mmol), KI (catalytic) and K2CO3(0.28 g, 2.0 mmol) after chromatographic purification as a white amorphous solid. 1H NMR (CDCl3, 300 MHz) δ 1.80–2.15 (m, 2H), 2.15–2.30 (m, 2H), 2.71 (t, J=7.0 Hz, 2H), 2.82 (d, J=5.1 Hz, 2H), 2.90 (t, J=5.8 Hz, 2H), 2.97 (t, J=6.1 Hz, 2H), 3.02–3.20 (m, 2H), 3.73 (s, 2H), 3.98 (t, J=5.7 Hz, 2H), 6.84 (d, J=6.9 Hz, 1H), 6.97 (t, J=7.5 Hz, 1H), 7.02–7.20 (m, 2H), 7.25 (d, J=7.7 Hz, 1H), 7.20–7.25 (m, 1H), 7.95–8.20 (m, 2H) ppm.

Workup

  1. customafter chromatographic purification as a white amorphous solid

Sources & evidence

ORD record
ord-2f60ee695f98447898537ff670b3426c
Source dataset
uspto-grants-2006_07
Patent number
US07081455B2

Reaction notes

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