Methanol → HCID 71295472, compound

HRID 1776806Notes

Reaction equation

HRID 1776806 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18]C)=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[C:14]([F:17])[CH:13]=[CH:12][CH:11]=3)[CH:7]=1.B(Br)(Br)Br.CO.O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[C:14]([F:17])[CH:13]=[CH:12][CH:11]=3)[CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 71295584HCID 71295584, compound

Product 1

HCID 71295472HCID 71295472, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-(5-chloro-2-methoxyphenyl)-4-fluoro-1H-indole (50 mg, 0.2 mmol) was dissolved in dichloromethane (1 mL), and then BBr3 (150 mg, 0.6 mmol) was added at −78° C. The mixture was stirred at −78° C. for 1 hour, and then stirred at 25° C. for 12 hours. MeOH (1 mL) and H2O (20 mL) were added to the solution. The mixture was extracted with ethyl acetate and washed with brine, dried over Na2SO4. After the combined organic layers were concentrated, the resulting residue was purified using prep-TLC (petroleum ether:EtOAc=5:1) to provide the product of 4-chloro-2-(4-fluoro-1H-indol-2-yl)phenol (10 mg, yield: 25%). 1H-NMR (CDCl3, 400 MHz) δ 9.54 (s, 1H), 7.65 (s, 1H), 7.06˜7.12 (m, 2H), 6.88 (s, 1H), 6.79˜6.81 (m, 1H), 6.70˜6.74 (m, 1H). MS (M+H)+: 262/263.

Workup

  1. stirringstirred at 25° C. for 12 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter the combined organic layers were concentrated
  6. customthe resulting residue was purified

Sources & evidence

ORD record
ord-b42b730027cb466cabf033e624a3346c
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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