Sodium Carbonate → 1-Benzenesulfonyl-5-(2,3-dihydro-benzofuran-5-yl)-3-(1-trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 2114063Notes

Reaction equation

HRID 2114063 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17](Br)[CH:18]=[C:13]3[C:12]([C:20]3[CH:21]=[N:22][N:23]([C:25]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:24]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:44]1[C:48]2[CH:49]=[CH:50][C:51](B(O)O)=[CH:52][C:47]=2[CH2:46][CH2:45]1.C([O-])([O-])=O.[Na+].[Na+].[Li+].[Cl-]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.CCO>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:51]4[CH:50]=[CH:49][C:48]5[O:44][CH2:45][CH2:46][C:47]=5[CH:52]=4)[CH:18]=[C:13]3[C:12]([C:20]3[CH:21]=[N:22][N:23]([C:25]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:24]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2773380(2,3-Dihydro-1-benzofuran-5-yl)boronic acidHCID 104167581-Benzenesulfonyl-5-bromo-3-(1-trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 670513901-Benzenesulfonyl-5-(2,3-dihydro-benzofuran-5-yl)-3-(1-trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 88.7%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 47 (200 mg, 0.308 mmol), EtOH (1.5 mL), toluene (1.5 mL), 2,3-dihydrobenzofuran-5-boronic acid (50 mg, 0.308 mmol), 1M aq. Na2CO3 (0.48 mL, 0.48 mmol), LiCl (25 mg, 0.619 mmol) and PdCl2(PPh3)2 (15 mg, 0.021 mmol) was refluxed for 1 h 40 min. The reaction mixture was concentrated to afford a pale yellow solid, which was purified by silicagel chromatography using 30% ethyl acetate in hexane as eluent (gradient elution) to give the product 48 (187 mg, 86%) as a pale yellow solid; 1H NMR (400 MHz, CDCl3) δ 3.27 (t, J=17.2, 8.6 Hz, 2H), 4.61 (t, J=17.4, 8.7 Hz, 2H), 6.86 (d, J=8.2 Hz, 1H), 7.19-7.23 (m, 7H), 7.33-7.36 (m, 10H), 7.45 (t, J=15.3, 7.26 Hz, 2H), 7.54-7.58 (m, 1H), 7.65 (s, 1H), 7.74 (s, 1H), 7.89 (d, J=2.1 Hz, 1H), 7.97 (s, 1H), 8.19-8.21 (m, 2H), 8.60 (d, J=2.1 Hz, 1H).

Workup

  1. temperaturewas refluxed for 1 h 40 min
  2. concentrationThe reaction mixture was concentrated
  3. customto afford a pale yellow solid, which
  4. customwas purified by silicagel chromatography
  5. wash(gradient elution)

Sources & evidence

ORD record
ord-3fffb229c8a24db292ea76de70a723db
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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