Potassium Carbonate → 4-[(10S,15R)-1,12-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-5(16),6,8-trien-12-yl]-1-(4-fluorophenyl)butan-1-one

HRID 1266115Notes

Reaction equation

HRID 1266115 reaction equation
[CH:1]1[C:10]2[C@H:11]3[CH2:16][NH:15][CH2:14][CH2:13][C@H: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+]>>[CH:1]1[C:10]2[C@H:11]3[CH2:16][N:15]([CH2:18][CH2:19][CH2:20][C:21]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)=[O:22])[CH2:14][CH2:13][C@H:12]3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 69433998(+/-)-cis-5,6,7a,8,9,10,11, 11a-octahydro-4H-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline

Product 1

HCID 694330764-[(10S,15R)-1,12-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-5(16),6,8-trien-12-yl]-1-(4-fluorophenyl)butan-1-oneYield 42.3%

Procedure

The title compound (0.16 g, 42%) was prepared by the general method of Example 402 from (7aR,11aS)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (0.21 g, 1.0 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. The 1H NMR was identical to that of Example 402, 4-((7aS,11aR)-5,6,8,9,11,11a-hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinolin-10(7aH)-yl)-1-(4-fluorophenyl)-1-butanone

Workup

  1. customafter chromatographic purification as a white amorphous solid

Sources & evidence

ORD record
ord-111303f53b5249368007fd4c691fff22
Source dataset
uspto-grants-2003_04
Patent number
US06548493B1

Reaction notes

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