Triisopropyl borate → HCID 57562462, compound

HRID 1776809Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[C:7]2[CH:9]=[CH:10][N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:6]2=[CH:5][CH:4]=1.[Li]C(C)(C)C.[B:24](OC(C)C)([O:29]C(C)C)[O:25]C(C)C>C1COCC1>[C:15]([O:14][C:12]([N:11]1[C:6]2[C:7](=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:9]=[C:10]1[B:24]([OH:29])[OH:25])=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of tert-butyl 5-methoxy-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (3 g, 12.08 mmol) in 40 mL of dry THF was added dropwise t-BuLi (1.16 g, 18.12 mmol) at −78° C. Then the solution was stirred at −78° C. for 1 hour. Then triisopropyl borate (4.55 g, 24.17 mmol) was added dropwise to the solution still at −78° C. The mixture was stirred at −78° C. for 2 hours and quenched the reaction with 1 M of HCl at low temperature to pH=3˜4. After it was extracted with EtOAc, the combined organic phase was washed with brine, dried over Na2SO4. After concentrated, the resulting residue was purified using column (petroleum ether:ethyl acetate=3:1) to provide (1-(tert-butoxycarbonyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)boronic acid (1.3 g, yield: 37%). 1H-NMR (CDCl3, 400 MHz) δ 8.10 (d, J=9.2 Hz, 1H), 7.46 (s, 1H), 6.88˜6.84 (m, 2H), 6.70 (d, J=9.2 Hz, 1H), 3.98 (s, 3H), 1.71 (s, 9H). MS (M+H)+: 293.

Workup

stirringThe mixture was stirred at −78° C. for 2 hours
customquenched
customthe reaction with 1 M of HCl at low temperature to pH=3˜4
extractionAfter it was extracted with EtOAc
washthe combined organic phase was washed with brine
dry with materialdried over Na2SO4
concentrationAfter concentrated
customthe resulting residue was purified

Sources & evidence

ORD record: ord-0cadaa826743452a914528f0ad78ae38
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265773B2

Reaction notes

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