Methanol → 1-Benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+].CO>C(Cl)Cl.[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O>[C:12]1([S:18]([N:8]2[C:5]3=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=[C:4]3[C:10]([I:11])=[CH:9]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a cooled solution of 45 (15.00 g, 46.6 mmol) in CH2Cl2 (210 mL) was added benzenesulfonyl chloride (9.18 mL, 71.8 mmol), 50% aq NaOH (13.04 mL) and Bu4NHSO4 (2.35 g, 6.94 mmol). The mixture was allowed to warm to ambient temperature and stirred for 2 h 45 min. The mixture was diluted with CH2Cl2 (200 mL) and washed with saturated brine solution (200 mL). The aqueous layer was extracted with CH2Cl2 (2×200 mL), the combined organics were dried (MgSO4) and concentrated to afford a pale yellow solid. The solid was stirred vigorously with cold methanol for 1 h and the resulting precipitate was filtered off and dried under vacuum to afford 46 as a white solid (20.90 g, 97%); 1H NMR (400 MHz, CDCl3) δ7.49 (t, J=15.5, 7.4 Hz, 2H), 7.60-7.64 (m, 1H), 7.81 (d, J=2.2 Hz, 1H), 7.87 (s, 1H), 8.17-8.19 (m, 2H), 8.45 (d, J=2.1 Hz, 1H).
Workup
- washwashed with saturated brine solution (200 mL)
- extractionThe aqueous layer was extracted with CH2Cl2 (2×200 mL)
- dry with materialthe combined organics were dried (MgSO4)
- concentrationconcentrated
- customto afford a pale yellow solid
- filtrationthe resulting precipitate was filtered off
- customdried under vacuum
Sources & evidence
- ORD record
- ord-b0455981b1304c0db447cc15699b8454
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432375B2
Reaction notes
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