Methanol → 3-phenyl-5-(2-hydroxyphenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 63600Notes

Reaction equation

HRID 63600 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[O:22]C)[CH:14]=3)[NH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[C:1]1([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[OH:22])[CH:14]=3)[NH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 727926883-phenyl-5-(2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 727928273-phenyl-5-(2-hydroxyphenyl)-1H-pyrrolo[2,3-b]pyridineYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-phenyl-5-(2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridine (113 mg, 0.38 mmol) in CH2Cl2 (325 μl) is added BBr3 (1.1 ml of 1 N solution in CH2Cl2, 1.13 mmol). The reaction mixture is stirred for 15 hours at room temperature and neutralized at 0° C. with methanol. The solvent is evaporated under reduced pressure and the residue purified by preparative thin-layer chromatography (CH2Cl2/MeOH 94:6) to yield the expected product in the form of a white solid with a yield of 34%.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. customthe residue purified by preparative thin-layer chromatography (CH2Cl2/MeOH 94:6)

Sources & evidence

ORD record
ord-d273fcfd4c7e4a19b268bc2796fea5f0
Source dataset
uspto-grants-2016_09
Patent number
US09447093B2

Reaction notes

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