1-Fluoro-2,6-dichloropyridinium Triflate → HCID 67155968, compound

HRID 2196717Notes

Reaction equation

[O-]S(C(F)(F)[F:6])(=O)=O.F[N+]1C(Cl)=CC=CC=1Cl.[F:18][C:19]1[C:36]([NH:37][S:38]([CH2:41][CH2:42][CH3:43])(=[O:40])=[O:39])=[CH:35][CH:34]=[C:33]([F:44])[C:20]=1[C:21]([NH:23][C:24]1[CH:25]=[C:26]2[CH:32]=[CH:31][NH:30][C:27]2=[N:28][CH:29]=1)=[O:22]>CC#N.CCOC(C)=O>[F:18][C:19]1[C:36]([NH:37][S:38]([CH2:41][CH2:42][CH3:43])(=[O:40])=[O:39])=[CH:35][CH:34]=[C:33]([F:44])[C:20]=1[C:21]([NH:23][C:24]1[CH:25]=[C:26]2[C:32]([F:6])=[CH:31][NH:30][C:27]2=[N:28][CH:29]=1)=[O:22]

Participants

Conditions

Temperature: 60 °C

Procedure

1-Fluoro-2,6-dichloropyridinium triflate (31 mg, 0.1 mmol) was added to 2,6-difluoro-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (39 mg, 0.1 mmol) in MeCN (4 mL). The mixture was heated at 60° C. for 18 hours and then cooled to room temperature. The mixture was then diluted with EtOAc, washed with brine, dried over MgSO4 and concentrated. The crude product was purified using silica gel chromatography (ISCO) using 5% MeOH in CH2Cl2 as eluent, and subsequently reverse phase HPLC to give 2,6-difluoro-N-(3-fluoro-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (10.7 mg, 26%). 1H NMR (400 MHz, d6-DMSO) δ 11.51 (s, 3H), 10.97 (s, 3H), 9.77 (s, 3H), 8.41 (s, 6H), 7.70-7.38 (m, 6H), 7.26 (t, J=8.5, 3H), 3.45-2.96 (m, 32H), 2.50 (s, 57H), 2.36-2.09 (m, 1H), 1.77 (dd, J=7.5, 15.1, 6H), 1.00 (t, J=7.4, 9H); m/z (LC-MS) M+1=413.4.

Workup

temperaturecooled to room temperature
washwashed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe crude product was purified

Sources & evidence

ORD record: ord-bee7837bd4484fb0a10218be4f50b4f3
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338452B2

Reaction notes

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