Acetonitrile → 4-chloro-6-(6-methyl-pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 1878613Notes

Reaction equation

HRID 1878613 reaction equation
Br[C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[C:4]([Cl:11])[CH:3]=1.[CH3:12][C:13]#[N:14]>CC1C=CC=C([Sn](CCCC)(CCCC)CCCC)N=1.C(OCC)C.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>[Cl:11][C:4]1[CH:3]=[C:2]([C:13]2[CH:12]=[CH:2][CH:3]=[C:4]([CH3:5])[N:14]=2)[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]=12

Participants

6

Reactant 2

HCID 6342AcetonitrileHCID 247295876-Bromo-4-chloro-1H-pyrrolo[2,3-B]pyridine

Product 1

HCID 687902414-chloro-6-(6-methyl-pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 114631832-Methyl-6-(tributylstannyl)pyridineSolvent

Procedure

To a solution of 6-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (1 eq, 11.0 mmol, 2.76 g) in MeCN (20 ml), 2-methyl-6-tributylstannanyl-pyridine (see Chemistry, A European Journal (2005), 11 (23), 6818-6828) (1 eq, 11.0 mmol, 4.19 g) and Pd(PPh3)4 (0.01 eq, 0.110 mmol, 131 mg) are added. The resulting mixture is heated using microwave radiation for 15 min at 160° C. The mixture is diluted with diethyl ether and extracted with aqueous HCl solution (2 M). The aqueous layer is basified with aqueous NaOH solution (4 M) and extracted with DCM. The organic layer is dried with MgSO4, filtered, and concentrated. The residue is taken up in hexane and stirred at r.t. for 1 h. The suspension is filtered and dried giving the title compound; [M+H]+=244.

Workup

  1. temperatureThe resulting mixture is heated
  2. customfor 15 min
  3. customat 160° C
  4. extractionextracted with aqueous HCl solution (2 M)
  5. extractionextracted with DCM
  6. dry with materialThe organic layer is dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. filtrationThe suspension is filtered
  10. customdried

Sources & evidence

ORD record
ord-fe753493e87047c18640a683fc65b60f
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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