Trifluoroacetic acid → HCID 12300190, compound

HRID 1445721Notes

Reaction equation

HRID 1445721 reaction equation
[OH:1][C:2]([C@@H:4]1[CH:19]=[C:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[NH:12][CH:11]=3)[N:6]([CH3:7])[CH2:5]1)=[O:3].C(O)(C(F)(F)F)=O.[Br:28]Br>O1CCOCC1.C(Cl)(Cl)Cl>[Br:28][C:11]1[NH:12][C:13]2[C:20]3[C:10]=1[CH2:9][C@@H:8]1[C:18](=[CH:19][C@@H:4]([C:2]([OH:1])=[O:3])[CH2:5][N:6]1[CH3:7])[C:17]=3[CH:16]=[CH:15][CH:14]=2

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 6717Lysergic AcidHCID 24408Bromine

Product 1

HCID 12300190HCID 12300190, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
5 °C

Procedure

Lysergic acid (8.05 g, 30 mmol) is suspended in dioxane and is treated with dropwise addition of TFA (exothermic). Bromine (1.54 ml, 30 mmol, 1.0 eq.) in chloroform is added dropwise. The reaction is cooled to 5° C. and product crystallizes. (6aR,9R)-5-Bromo-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid is isolated by filtration and re-crystallised from diethylether. Rf=0.5, 10% MeOH:DCM, M+H+=346, 348, m.p.>245 (decomposition).

Workup

  1. customproduct crystallizes

Sources & evidence

ORD record
ord-1efb07e85d18488ab72754eb8a2e7391
Source dataset
uspto-grants-2010_02
Patent number
US07666877B2

Reaction notes

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