3-Chloroaniline → 1H,4H,5H,6H,7H-pyrrolo[3,2-c]pyridin-4-one

HRID 1055870Notes

Reaction equation

ClC1C=C(C=CC=1)N.ClC1C=CC2C(=C([C:20]3[NH:28][C:27]4[CH2:26][CH2:25][NH:24][C:23](=[O:29])[C:22]=4[CH:21]=3)C=CC=2)N=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1>>[NH:28]1[C:27]2[CH2:26][CH2:25][NH:24][C:23](=[O:29])[C:22]=2[CH:21]=[CH:20]1

Participants

Reactant 4

HCID 79323-Chloroaniline

HCID 8028Tetrahydrofuran

HCID 2733832Lithium Hexamethyldisilazide

HCID 897835482-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 220385131H,4H,5H,6H,7H-pyrrolo[3,2-c]pyridin-4-oneYield 47.2%

Procedure

Prepared according to Example 102, using 3-chloroaniline (220 μl, 2.099 mmol, Sigma Aldrich), 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 125 mg, 0.420 mmol). and 1.0 M LHMDS, 1.0M in THF (2099 μl, 2.099 mmol, Sigma Aldrich) and stirring at 25° C. for 30 min. Purification by column chromatography (silica gel 1 to 5% MeOH/DCM) provided 2424(3-chlorophenyl)amino)-8-quinolinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (27 mg, 16.5%). 1H NMR (400 MHz, CDCl3) δ ppm 12.09-12.31 (1H, m) 8.03 (2H, d, J=1.00 Hz) 7.57-7.60 (1H, m) 7.50-7.55 (1H, m) 7.33-7.41 (4H, m) 7.17-7.22 (1H, m) 7.12-7.15 (1H, m) 6.88-6.93 (1H, m) 5.23-5.28 (1H, m) 3.55-3.62 (2H, m) 2.67-2.73 (2H, m). m/z (ESI, +ve) 389.1 (M+H)+.

Workup

customPrepared
customPurification by column chromatography (silica gel 1 to 5% MeOH/DCM)

Sources & evidence

ORD record: ord-98b2ff9e6bc340b6adc8a38df7be2de6
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

Loading…