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

HRID 2196717
Notes
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Reaction equation

HRID 2196717 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 27373111-Fluoro-2,6-dichloropyridinium TriflateHCID 441994082,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide

Product 1

HCID 67155968HCID 67155968, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl Acetate
Solvent

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

  1. temperaturecooled to room temperature
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes