Dichloromethane → 3-(5-Thiophen-3-yl-1H-pyrrolo[2,3-b]pyridine-3-ylmethyl)-phenol

HRID 1785586Notes

Reaction equation

HRID 1785586 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:16]3[CH:20]=[CH:19][S:18][CH:17]=3)[CH:14]=2)[NH:9][CH:8]=1.C(Cl)Cl.B(Br)(Br)Br>O>[S:18]1[CH:19]=[CH:20][C:16]([C:13]2[CH:14]=[C:15]3[C:7]([CH2:6][C:5]4[CH:4]=[C:3]([OH:2])[CH:23]=[CH:22][CH:21]=4)=[CH:8][NH:9][C:10]3=[N:11][CH:12]=2)=[CH:17]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 111629973-(3-Methoxy-benzyl)-5-thiophen-3-yl-pyrrolo[2,3-b]pyridine

Product 1

HCID 113012233-(5-Thiophen-3-yl-1H-pyrrolo[2,3-b]pyridine-3-ylmethyl)-phenolYield 26.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a Round bottom flask was added compound 14 (20.0 mg, 0.0000624 mol) and Methylene chloride (4.0 mL, 0.062 mol) at room temperature. Into the reaction mixture, was added 0.1 mL BBr3 (1.0M in). The reaction mixture was allowed to room temperature for 5 hours. TLC indicated the reaction was not complete. The reaction mixture was poured into water, extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified with preparative TLC to give product 15 (5 mg).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified with preparative TLC

Sources & evidence

ORD record
ord-85b82fd38f6d4cab867a7ba10387a77a
Source dataset
uspto-grants-2009_03
Patent number
US07504509B2

Reaction notes

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