7-Bromoindole → HCID 69020213, compound

HRID 1865088Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:29])[C:8](CC)=[C:9]([C:25]#[N:26])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14](OS(C(F)(F)F)(=O)=O)=[CH:13][CH:12]=1)=[O:5])[CH3:2].Br[C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:39]=1[NH:38][CH:37]=[CH:36]2>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:29])[CH:8]=[C:9]([C:25]#[N:26])[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([C:31]2[CH:32]=[CH:33][CH:34]=[C:35]3[C:39]=2[NH:38][CH:37]=[CH:36]3)=[CH:15][CH:16]=1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 27570207-Bromoindole

HCID 57974728HCID 57974728, compound

Product 1

HCID 69020213HCID 69020213, compound

Procedure

Prepare the title compound in the manner analogous to the procedure set fourth in example E-222 using 4-cyano-5-ethyl-1-methyl-3-(4-trifluoromethanesulfonyloxyphenyl)-1H-pyrrole-2-carboxylic acid ethyl ester (prepared in example E-97a or 97b) and 7-bromo-indole. Purify the material by silica gel chromatography eluting with hexanes/ethyl acetate 4:1 to provide the title compound as a white solid. Mass spectrum (m/e): 398.25 (M*+1).

Workup

customPurify the material by silica gel chromatography
washeluting with hexanes/ethyl acetate 4:1

Sources & evidence

ORD record: ord-90739a8d5e1b436f96439eab861a4260
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625932B2

Reaction notes

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