Sodium Chloride → N1,N1-dimethyl-N2-(1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)ethane-1,2-diamine

HRID 1025643Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]2[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH2:25].CC(C)([O-])C.[Na+].[Na+].[Cl-]>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1(C)C=CC=CC=1>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH:25][C:2]1[N:7]=[C:6]2[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a 25 mL round-bottomed flask, 6-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (713 mg, 2.02 mmol, Eq: 1.00), N,N-dimethylethylenediamine (1.07 g, 1.32 ml, 12.1 mmol, Eq: 6) and bis(tri-tert-butylphosphine)palladium(0) (206 mg, 404 μmol, Eq: 0.2) were combined with toluene (2 ml) to give a yellow solution. Sodium tert-butoxide (582 mg, 6.05 mmol, Eq: 3) was added. The reaction mixture was heated to 80° C. and stirred for 1 h, then poured into 20 mL sat NaCl and extracted with EtOAc (3×20 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 12 g, 2% to 5% MeOH in DCM) to give N1,N1-dimethyl-N2-(1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)ethane-1,2-diamine (405 mg, 56%) as yellow oil that solidified upon standing.

Workup

customto give a yellow solution
additionpoured into 20 mL
extractionextracted with EtOAc (3×20 mL)
dry with materialThe organic layers were dried over MgSO4
concentrationconcentrated in vacuo
customThe crude material was purified by flash chromatography (silica gel, 12 g, 2% to 5% MeOH in DCM)

Sources & evidence

ORD record: ord-01e1cba6899b4996a033dce7a64995e3
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729078B2

Reaction notes

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