1-Propanol → HCID 24743834, compound

HRID 641867Notes

Reaction equation

HRID 641867 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH:15]=[C:14]2[C:29]1[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH:34]=1.C(O)CC.C([O-])([O-])=O.[Na+].[Na+]>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:35][N:32]1[CH2:33][CH:34]=[C:29]([C:14]2[C:13]3[C:17](=[CH:18][CH:19]=[C:11]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)[CH:12]=3)[N:16]([S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:15]=2)[CH2:30][CH2:31]1

Participants

7

Reactant 4

HCID 10311-PropanolHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 534150661-(Benzenesulfonyl)-5-bromo-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 24743834HCID 24743834, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Into a 100 mL 3-necked round bottom flask was placed pyridin-3-ylboronic acid (200 mg, 1.63 mmol), 5-bromo-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(phenylsulfonyl)-1H-indole (470 mg, 1.08 mmol), and n-propanol (140 mL). The mixture was stirred at room temperature for 30 min during which time the solids dissolved. A solution of Na2CO3 (430 mg, 4.06 mmol) in water (5 mL) was then added, followed by the addition of Pd(PPh3)4 (130 mg, 0.108 mmol). The resulting solution was stirred at reflux temperature overnight, and then concentrated. The residue was dissolved in water (10 mL), and the resulting solution was extracted diethylether (2×50 mL). The organic layers were combined and the residue was purified by column chromatography using a 1:5 dichloromethane/methanol solvent system to afford 200 mg (42.5%) of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(phenylsulfonyl)-5-(pyridin-4-yl)-1H-indole as a deep yellow solid. 1H NMR (CDCl3) δ 8.69 (d, 2H), 8.12 (d, 1H), 7.93 (t, 3H), 7.60 (d, 3H), 7.48 (d×d, 4H), 6.18 (s, 1H), 2.85 (2H), 1.52 (2H), 1.25 (3H), 0.87 (2H). LC/MS (EI) tR 2.18, m/z 430.0 (M++1)

Workup

  1. customInto a 100 mL 3-necked round bottom flask was placed
  2. dissolutiondissolved
  3. stirringThe resulting solution was stirred
  4. temperatureat reflux temperature overnight
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in water (10 mL)
  7. extractionthe resulting solution was extracted diethylether (2×50 mL)
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c436c1a9fcae416385e30e8c5e688755
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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