Sodium Carbonate → HCID 21716630, compound

HRID 1385994Notes

Reaction equation

HRID 1385994 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[CH:7]=1.[S:13]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](B(O)O)=[CH:24]1)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[S:10]1[CH:11]=[CH:12][C:8]([C:6]2[CH:7]=[C:2]([C:25]3[C:26]4[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:23]([S:13]([C:16]4[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=4)(=[O:15])=[O:14])[CH:24]=3)[CH:3]=[N:4][CH:5]=2)=[CH:9]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 3857443N-(p-Toluenesulfonyl)indole-3-boronic acidHCID 112764923-Bromo-5-thiophen-3-yl-pyridine

Product 1

HCID 21716630HCID 21716630, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A deoxygenated solution of 3-bromo-5-thiophen-3-yl-pyridine (250 mg, 1.04 mmol, 1 equiv), 1-tosyl-3-indoleboronic acid (430 mg, 1.36 mmol, 1.31 equiv, prepared according to Zheng, Q; Yang, Y; Martin, A. R. Heterocycles 1994, 37, 1761), Pd(PPh3)4 (60 mg, 0.052 mmol, 0.050 equiv), and 2.0 M Na2CO3 (1.0 mL, 2.0 mmol, 1.9 equiv) in dioxane (10 ml) was heated under argon at reflux for 20 h. The reaction mixture was allowed to cool, then partitioned between water (100 mL) and ethyl acetate (2×100 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (40% ethyl acetate in hexane) to afford 3-(5-thiophen-3-yl-pyridin-3-yl)-1-(toluene-4-sulfonyl)-indole as a white foam.

Workup

  1. temperatureat reflux for 20 h
  2. temperatureto cool
  3. custompartitioned between water (100 mL) and ethyl acetate (2×100 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-941b6e0d85574b52853e53a192d2c720
Source dataset
uspto-grants-2001_07
Patent number
US06265403B1

Reaction notes

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