Pentane → HCID 59578424, compound

HRID 2407425Notes

Reaction equation

HRID 2407425 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-003c9f0de7ac4dee91d6ae24dcf5c3f1
Source dataset
uspto-grants-2014_08
Patent number
US08809545B2

Reaction notes

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