Hydrochloric Acid → HCID 68328688, compound

HRID 634118Notes

Reaction equation

HRID 634118 reaction equation
I[C:2]1[C:6]2=[N:7][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:10]=[C:5]2[N:4]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:3]=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:30]=[N:31][CH:32]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Cl>CC(O)C.O>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([C:2]2[C:6]3=[N:7][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:10]=[C:5]3[N:4]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:3]=2)[CH:30]=[N:31][CH:32]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 38661613-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 68328196HCID 68328196, compound

Product 1

HCID 68328688HCID 68328688, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A glass microwave reaction vessel was charged with methyl 3-iodo-1-((4-methylphenyl)sulfonyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylate (0.300 g, 0.658 mmol), 5-methoxy-3-pyridineboronic acid pinacol ester (0.216 g, 0.921 mmol, Sigma-Aldrich), and K3PO4 (0.419 g, 1.973 mmol) in 70% i-PrOH in H2O (3.30 mL). The reaction was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 100° C. for 10 min. 2 M HCl (aq.) was added and the mixture was extracted with DCM (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude material was absorbed onto a plug of silica gel and purified by column chromatography (eluting with 0-10% MeOH in DCM) to provide methyl 3-(5-methoxy-3-pyridinyl)-1-((4-methylphenyl)sulfonyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylate (0.170 g, 0.389 mmol, 59.1%) as a pale yellow solid. MS (ESI, pos. ion) m/z: 438.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 2.37 (3H, s), 3.96 (3H, s), 4.00 (3H, s), 7.29 (2H, d, J=8.22 Hz), 7.79-7.85 (2H, m), 8.16-8.21 (2H, m), 8.27-8.34 (2H, m), 8.42 (1H, d, J=8.61 Hz), 8.81 (1H, d, J=1.56 Hz).

Workup

  1. customA glass microwave reaction vessel
  2. extractionthe mixture was extracted with DCM (3×)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was absorbed onto a plug of silica gel
  7. custompurified by column chromatography (eluting with 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-498c5e7659ed4aaf8ba1ab17121fe6ed
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

Loading…