Benzyl Alcohol → HCID 89783920, compound

HRID 1055856Notes

Reaction equation

HRID 1055856 reaction equation
[H-].[Na+].[C:3]1([CH2:9][OH:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[C:15]([C:22]3[NH:30][C:29]4[CH2:28][CH2:27][NH:26][C:25](=[O:31])[C:24]=4[CH:23]=3)[CH:16]=[CH:17][CH:18]=2)[N:13]=1>CN(C=O)C>[CH2:9]([O:10][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[C:15]([C:22]3[NH:30][C:29]4[CH2:28][CH2:27][NH:26][C:25](=[O:31])[C:24]=4[CH:23]=3)[CH:16]=[CH:17][CH:18]=2)[N:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 897835482-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89783920HCID 89783920, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

NaH (60% in mineral oil; 0.071 g, 1.763 mmol) was suspended in 1 mL DMF. Phenylmethanol (0.183 ml, 1.763 mmol) was added slowly dropwise. After 10 min, 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 0.075 g, 0.252 mmol) was added, and the reaction was heated to 100° C. for 30 min. The mixture was cooled and partitioned between saturated aq. NH4Cl and DCM. The aq. layer was extracted with DCM (3×), and the combined organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The material was treated with DCM and purified by silica gel chromatography using 0-100% 90/10 DCM/MeOH in DCM The product-containing fractions were concentrated to afford 2-(2-(benzyloxy)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.018 g, 0.049 mmol, 19% yield) as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.76 (1H, br. s), 8.32 (1H, d, J=9.0 Hz), 8.00 (1H, dt, J=7.2, 1.0 Hz), 7.76 (1H, dt, J=7.9, 0.8 Hz), 7.26-7.59 (6H, m), 7.10-7.22 (2H, m), 6.87-6.99 (1H, m), 5.62 (2H, s), 3.36-3.51 (2H, m), 2.86 (2H, t, J=6.9 Hz). m/z (ESI, +ve) 370.0 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between saturated aq. NH4Cl and DCM
  3. extractionThe aq. layer was extracted with DCM (3×)
  4. dry with materialthe combined organics were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThe material was treated with DCM
  8. custompurified by silica gel chromatography
  9. concentrationwere concentrated

Sources & evidence

ORD record
ord-44b62cc1b2474b499978378ee935137e
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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