Dimethyl acetylenedicarboxylate → HCID 70300726, compound

HRID 1422120Notes

Reaction equation

[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([CH2:25][CH3:26])=[C:18]3[N:23]([CH:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19]3)=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:27]([C:33]([O:35][CH3:36])=[O:34])#[C:28][C:29]([O:31][CH3:32])=[O:30]>>[CH2:25]([C:17]1[C:18]2[N:23]3[C:22]([CH:21]=[CH:20][CH:19]=2)=[C:28]([C:29]([O:31][CH3:32])=[O:30])[C:27]([C:33]([O:35][CH3:36])=[O:34])=[C:24]3[C:16]=1[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])=[CH:11][CH:12]=1)[CH3:26]

Participants

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylate

HCID 18707011HCID 18707011, compound

Product 1

HCID 70300726HCID 70300726, compound

Procedure

2-(4-(tert-Butyldimethylsilanyloxymethyl)phenyl)-1-ethylindolizine prepared in example 97, step 2, was reacted with dimethyl acetylene dicarboxylate by the general synthetic principle outlined in example 23, step 6, to afford dimethyl 4-ethyl-3-(4-(tert-butyldimethylsilanyloxymethyl)phenyl)pyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate, which was hydrolysed and desilylated by the general synthetic principle outlined in example 23, step 7, to afford 4-ethyl-3-(4-hydroxymethylphenyl)pyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid as yellow crystals in 63% yield. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.35 (t, 3H); 3.11 (q, 2H); 4.61 (d, 2H); 7.50 (d, 2H); 7.61 (d, 2H); 8.03 (dd, 1H); 8.32 (d, 1H); 8.42 (d, 1H).

Sources & evidence

ORD record: ord-0027fe59228b498cb51ad7c746efab4c
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06080754

Reaction notes

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