Pentane → HCID 59578424, compound

HRID 1897796Notes

Reaction equation

HRID 1897796 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[Li]C(C)(C)C.CCCCC.[B:22](OC)([O:25]C)[O:23]C>C1COCC1.O>[Cl:1][C:2]1[N:7]=[C:6]2[C:5]([CH:10]=[C:9]([B:22]([OH:25])[OH:23])[N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8003PentaneHCID 8470Trimethyl borateHCID 21360855HCID 21360855, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 59578424HCID 59578424, compoundYield 163.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 6-chloro-1-methyl-1H-pyrrolo[2,3-b]pyridine (1.02 g, 6.12 mmol)) in THF (60 mL) at −78° C. was added 1.7 M t-BuLi in pentane (9.00 mL, 15.31 mmol) and the mixture was stirred at −78° C. for 2 h. Trimethyl borate (1.026 mL, 9.18 mmol) was added at −78° C. and the mixture was allowed to warm to room temperature, and stirred at room temperature overnight. Water (2 mL) was added and the mixture was concentrated in vacuo. The solid was subjected to high vacuum overnight to afford 2.1 g of 6-chloro-N-methyl-7-aza indole-2-boronic acid. ESI-MS: m/z 211.1 (M+H)+

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred at room temperature overnight
  3. concentrationthe mixture was concentrated in vacuo
  4. customwas subjected to high vacuum overnight

Sources & evidence

ORD record
ord-b254c8d8f5a34e8f9e1eaef69372e0ef
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

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