1,1'-Carbonyldiimidazole → HCID 19608782, compound

HRID 1603041Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([C:14]([OH:16])=O)[CH:8]=2)=[O:4].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([C:14]([NH:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)=[O:16])[CH:8]=2)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-(methoxycarbonyl)indole-6-carboxylic acid (290 mg, 1.32 mmol) and 1,1'-carbonyldiimidazole (257 mg, 1.59 mmol) in THF (20 mL) was stirred at reflux for 1 h then cooled and evaporated. A solution of 2-(2-aminoethyl)pyridine (0.19 mL, 1.6 mmol) in DMF (5 mL) was added and the mixture stirred at 80° C. for 2 h, then cooled and evaporated. Trituration with hot EtOAc gave 2-(methoxycarbonyl)-N-[2-(2-pyridinyl)ethyl]indole-6-carboxamide as a white solid (360 mg, 84%), mp 191-193° C. 1H NMR [(CD3)2SO] δ12.24 (s, 1H, indole NH), 8.61 (t, J=5.5 Hz, 1H, amide NH), 8.54-8.50 (m, 1H, H-6'), 7.97 (s, 1H, H-3 or H-7), 7.71 (td, J=7.6, 1.8 Hz, 1H, H-4'), 7.70 (d, J=8.6 Hz, 1H, H-4), 7.55 (dd, J=8.6, 1.4 Hz, 1H, H-5), 7.29 (d, J=7.8 Hz, 1H, H-3'), 7.23 (ddd, J=7.4, 4.8, 0.8 Hz, 1H, H-5'), 7.20 (s, 1H, H-3 or H-7), 3.90 (s, 3H, CO2Me), 3.64 (q, J=6.8 Hz, 2H, NHCH2CH2 py), 3.03 (t, J=7.4 Hz, 2H, NHCH2CH2 py); 13C NMR δ166.6 (CONH), 161.5 (CO2Me), 159.2 (C-2'), 136.7, 131.0, 129.1, 128.5 (C-2,6,8,9), 149.0, 136.4, 123.1, 121.6, 121.4, 118.9, 112.2, 107.5 (C-3,4,5,7,3',4',5',6'), 51.9 (OCH3), 39.3, 37.3 (NHCH2CH2 py). Anal. (C18H17N3O3) C,H,N.

Workup

temperatureat reflux for 1 h
temperaturethen cooled
customevaporated
temperaturecooled
customevaporated

Sources & evidence

ORD record: ord-637c7a472ec64a9d89dfc20455629add
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05985909

Reaction notes

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