Hydrochloric Acid → (4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-2-yl)boronic acid

HRID 347529Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][C:3]=12.[Li]CCCC.C([O:27][B:28](OC(C)C)[O:29]C(C)C)(C)C.Cl.OP([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:9]([B:28]([OH:29])[OH:27])=[CH:10][C:3]=12

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of 4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (565 mg, 2 mmol) in THF (5 mL) at −40° C. under N2, was added n-BuLi (2.0 M in cyclohexane, Aldrich, 2.4 mmol). The reaction mixture was stirred at −40° C. for 1 h and then treated with triisopropylborate (489 mg, 2.6 mmol). The mixture was slowly warmed to rt and stirred overnight. To this solution was added 1 N HCl in H2O (20 mL), and the mixture was stirred for 20 min., neutralized with saturated aq. K2HPO4 solution and extracted with ether. The organic layer was dried over Na2SO4. After filtration and concentration under reduced pressure, the title compound was obtained as a light beige solid (640 mg, quantitative yield). LC/MS(ESI+) m/z 327 (M+H)+.

Workup

temperatureThe mixture was slowly warmed to rt
stirringstirred overnight
stirringthe mixture was stirred for 20 min.
extractionextracted with ether
dry with materialThe organic layer was dried over Na2SO4
filtrationAfter filtration and concentration under reduced pressure

Sources & evidence

ORD record: ord-81d53db54a5c48bf9789e8a913efefab
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173031B2

Reaction notes

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