2,6-Difluorophenol → HCID 89783570, compound

HRID 1055988Notes

Reaction equation

HRID 1055988 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]3[NH:20][C:19]4[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=4[CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[OH:30]>>[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[O:30][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]3[NH:20][C:19]4[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=4[CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 943922,6-DifluorophenolHCID 897835482-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89783570HCID 89783570, compoundYield 54%

Conditions

Temperature
120 °C

Procedure

Prepared in a manner similar to that described in Example 79 using 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 61 mg, 0.205 mmol) and 2,6-difluorophenol (133 mg, 1.024 mmol, Aldrich) and heating at 120° C. for 5 min in a microwave (Biotage Initiator). Purification by silica gel (100% DCM to 20% MeOH/DCM) provided 2-(2-(2,6-difluorophenoxy)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (54% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.51-2.57 (m, 2H) 3.34-3.39 (m, 2H) 6.86 (d, J=2.35 Hz, 1H) 6.91 (br. s., 1H) 7.40-7.47 (m, 2H) 7.48-7.54 (m, 1H) 7.55 (d, J=1.96 Hz, 1H) 7.57 (s, 1H) 7.87 (dd, J=8.02, 0.98 Hz, 1H) 8.11 (dd, J=7.43, 1.17 Hz, 1H) 8.58 (d, J=9.00 Hz, 1H) 10.96 (br. s., 1H). 19F NMR (376 MHz, DMSO-d6) δ ppm −126.54 (2F, s). MS (ESI, pos. ion) m/z: 392.1 (M+1).

Workup

  1. customPrepared in a manner similar to
  2. customPurification by silica gel (100% DCM to 20% MeOH/DCM)

Sources & evidence

ORD record
ord-80c3df20805544658da1277898bc68b8
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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