Boron tribromide → HCID 49855057, compound

HRID 1503116Notes

Reaction equation

HRID 1503116 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2/[C:12](=[CH:15]/[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)/[C:13]#[N:14].C(=O)=O.C(O)C.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2/[C:12](=[CH:15]/[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)/[C:13]#[N:14]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 19604758Methanedione--ethanol (1/1)HCID 49831238HCID 49831238, compound2×

Product 1

HCID 49855057HCID 49855057, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of (Z)-2-(5-methoxy-1H-indol-3-yl)-3-pyridin-3-yl-acrylonitrile (compound of example 4) (175 mg, 0.6 mmol, 1.0 eq.) in anhydrous dichloromethane (2 mL) cooled to −78° C. (dry ice/ethanol bath) was added, under an argon atmosphere, a 1M boron tribromide solution in dichloromethane (2 mL, 2.0 mmol, 3.2 eq.). The reaction mixture was stirred at ambient temperature for 18 hours and then quenched with ethanol. The solvent was removed under reduced pressure and the residue purified by silica gel flash-column chromatography (eluent: CH2Cl2/MeOH, 95:5 to 93:7) to afford (Z)-2-(5-hydroxy-1H-indol-3-yl)-3-pyridin-3-yl-acrylonitrile as a yellow powder (150 mg, 91%).

Workup

  1. additionwas added, under an argon atmosphere
  2. customquenched with ethanol
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by silica gel flash-column chromatography (eluent: CH2Cl2/MeOH, 95:5 to 93:7)

Sources & evidence

ORD record
ord-c4a2f940ff924e9ba52874fde2064892
Source dataset
uspto-grants-2015_12
Patent number
US09212138B2

Reaction notes

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