Boron tribromide → HCID 86728225, compound

HRID 1776795Notes

Reaction equation

HRID 1776795 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[N:11]=[C:10]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:9]([O:21]C)=[CH:8][CH:7]=1>C(Cl)Cl>[Cl:5][C:6]1[N:11]=[C:10]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:9]([OH:21])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86728224HCID 86728224, compound

Product 1

HCID 86728225HCID 86728225, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (0.4 mL, 0.39 mmol) was added to the solution of 2-(6-chloro-3-methoxypyridin-2-yl)-1H-indole (50 mg, 0.19 mmol) in CH2Cl2 (0.5 mL) at −78° C. under N2. The mixture was allowed to stir at room temperature for 3 hours. The mixture was then quenched with CH3OH (10 mL) at −78° C. After being concentrated in vacuo, the resulting resulting residue was purified using prep-TLC (petroleum ether:EtOAc=2.5:1) to provide 6-chloro-2-(1H-indol-2-yl)pyridin-3-ol (40 mg, yield: 85.1%), which was also prepared from 6-chloro-2-iodopyridin-3-ol and (1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid using similar procedure of step 3 of Example 1. 1H-NMR (CDCl3, 400 MHz) δ 10.09 (s, 1H), 9.72 (s, 1H), 7.50 (d, J=7.9 Hz, 1H), 7.17˜7.32 (m, 3H), 7.08˜7.14 (m, 1H), 6.87˜6.96 (m, 2H). MS (M+H)+: 245/247.

Workup

  1. customThe mixture was then quenched with CH3OH (10 mL) at −78° C
  2. concentrationAfter being concentrated in vacuo
  3. customthe resulting resulting residue
  4. customwas purified

Sources & evidence

ORD record
ord-86a3fc361ee44eb9b3180c32fee78406
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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