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

HRID 1055875Notes

Reaction equation

HRID 1055875 reaction equation
FC1C=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

5

Reactant 4

HCID 8028TetrahydrofuranHCID 97423-FluoroanilineHCID 2733832Lithium HexamethyldisilazideHCID 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 121.9%

Procedure

Prepared according to Example 102, using 3-fluoroaniline (230 μl, 2.069 mmol, Sigma Aldrich), 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 77 mg, 0.259 mmol), and 1.0 M LHMDS, in THF (2069 μl, 2.069 mmol, Sigma Aldrich) and stirring at 25° C. for 30 min. Purification by column chromatography (silica gel: 0 to 100% EtOAc/hexanes) provided 2424(3-fluorophenyl)amino)-8-quinolinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (43 mg, 44.6%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.91-12.00 (m, 1H) 9.69-9.77 (1H, m) 8.14-8.21 (1H, m) 7.87-7.93 (2H, m) 7.62-7.77 (3H, m) 7.31-7.54 (2H, m) 7.08-7.16 (2H, m) 6.78-6.89 (1H, m) 3.38-3.50 (2H, m) 2.67-2.76 (2H, m). m/z (ESI, +ve) 373.1 (M+H)+.

Workup

  1. customPrepared
  2. customPurification by column chromatography (silica gel: 0 to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-24394d4403f04a96a465e8dd78baeb22
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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