Trifluoroacetic acid → 4-(4-benzyloxy-phenoxy)-1H-pyrrolo[2,3-b]pyridine

HRID 491667Notes

Reaction equation

HRID 491667 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(C(F)(F)F)=O>CCN(CC)CC>[CH2:11]([O:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[NH:8][CH:9]=[CH:10][C:3]=23)=[CH:23][CH:24]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7638MonobenzoneHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 177555034-(4-benzyloxy-phenoxy)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine (1 g, 6.5 mmol), 4-benzyloxyphenol (1.5 g, 7.5 mmol) and Et3N:TFA (1.2 mL) was heated to 150° C. for 96 h. Formation of the compound was monitored by HPLC-mass spec. The crude was directly purified on silica gel without work-up using a Hexanes/EtOAc gradient (100/0 to 0/100) to afford 4-(4-benzyloxy-phenoxy)-1H-pyrrolo[2,3-b]pyridine.

Workup

  1. customThe crude was directly purified on silica gel without work-up

Sources & evidence

ORD record
ord-be345b88a0284401b93fa7a2dd8847b7
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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