Sodium Carbonate → HCID 59596028, compound

HRID 2264232Notes

Reaction equation

HRID 2264232 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[C:12](B3OC(C)(C)C(C)(C)O3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:28][C:29]1[N:34]=[C:33](Cl)[CH:32]=[CH:31][N:30]=1.C([O-])([O-])=O.[Na+].[Na+]>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.COCCOC>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[C:12]([C:31]3[CH:32]=[CH:33][N:34]=[C:29]([Cl:28])[N:30]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 455881371-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine

Product 1

HCID 59596028HCID 59596028, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of compound 1e (15.00 g), 2,4-dichloropyrimidine (7.56 g) and tetrakis(triphenylphosphine)palladium(0) (4.51 g) in a solution of ethylene glycol dimethyl ether (200 mL) and aqueous Na2CO3 (2M, 60 mL) was refluxed overnight. The reaction was quenched with water and extracted with ethyl acetate. The combined organic phase was concentrated and the residue was purified on silica gel column (eluted with 100% dichloromethane and 3% acetone in dichloromethane) to provide 1-benzenesulfonyl-3-(2-chloro-pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine (1f) (7.83 g, 54%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.78 (d, J=8.0 Hz, 1H), 8.62 (d, J=5.6 Hz, 1H), 8.52 (d, J=4.8 Hz, 1H), 8.47 (s, 1H), 8.28 (d, J=7.6 Hz, 2H), 7.63 (t, J=7.6 HZ, 1H), 7.57 (d, J=5.2 Hz, 1H), 7.53 (t, J=8.0 Hz, 2H), 7.35 (dd, J=8.0 Hz, 4.8 Hz, 1H). MS (ESI) m/z: 371 (M+H)+.

Workup

  1. temperaturewas refluxed overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. concentrationThe combined organic phase was concentrated
  5. customthe residue was purified on silica gel column (eluted with 100% dichloromethane and 3% acetone in dichloromethane)

Sources & evidence

ORD record
ord-2bd3b6329bf64004a69c9702f3cc5093
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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