Dimethyl acetylenedicarboxylate → HCID 68914640, compound

HRID 1958517Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-methoxy-1-(4′-methoxybenzoyl)-2,3-dihydro-1H-indole-2-carboxylic acid (4.24 g, 12.9 mmol) and dimethyl acetylenedicarboxylate (2.4 mL, 19.5 mmol) in acetic anhydride (24 mL) was heated for 4.5 hours at 120° C. until no gas eliminated. The dark solution was concentrated in vacuo to dryness and the solid residue was recrystallized from methanol to yield 6-methoxy-3-(4-methoxy-phenyl)-8H-3a-azacyclopenta[a]indene-1,2-dicarboxylic acid dimethyl ester, 3.75 g (71%): mp 240-242° C.; 1H NMR (DMSO-d6) δ 3.60 (3H, s, COOMe), 3.73 and 3.77 (each 3H, s, 2×OMe), 3.85 (3H, s, COOMe), 4.09 (2H, s, CH2), 6.55 (1H, d, J=8.8 Hz, ArH), 6.77 (1H, dd, J=2.6 Hz and J=8.8 Hz, ArH), 7.08 (2H, d, J=8.7 Hz, 2×ArH), 7.19 (1H, d, J=2.4 Hz, ArH), 7.42 (2H, d, J=8.7 Hz, 2×ArH). Anal. Calcd. for C23H21NO5: C, 67.84; H, 5.20; N, 3.44. Found: C, 67.83; H, 5.19; N, 3.39.

Workup

concentrationThe dark solution was concentrated in vacuo to dryness
customthe solid residue was recrystallized from methanol

Sources & evidence

ORD record: ord-215ed57a127d4d2aaf08e948c13694bd
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410130B2

Reaction notes

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