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

HRID 491687Notes

Reaction equation

Cl[C:2]1[CH:10]=[CH:9][N:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[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>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:11]([O:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][C:2]2[CH:10]=[CH:9][N:8]=[C:7]3[NH:6][CH:5]=[CH:4][C:3]=23)=[CH:23][CH:24]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a N2 purged round bottom flask was added 4-chloro-7-azaindole (15.8 g, 104 mmol, 1.0 eq.) followed by 4-benzyloxyphenol (41.5 g, 207 mmol, 2.0 eq), 20 ml of TFA/Et3N (1/1, 107 mmol, 1.0 eq.) and DMAP (13 g, 106 mmol, 1.0 eq.). The reaction was heated to 140° C. for 48 h. The mixture was cooled to RT and diluted with CH2Cl2 (100 mL) Silica gel was added and the mixture was evaporated to dryness onto the silica. The crude mixture was purified by column chromatography (20-100% EtOAc/Hexane) to give 4-(4-benzyloxy-phenoxy)-1H-pyrrolo[2,3-b]pyridine.

Workup

temperatureThe mixture was cooled to RT
additionwas added
customthe mixture was evaporated to dryness onto the silica
customThe crude mixture was purified by column chromatography (20-100% EtOAc/Hexane)

Sources & evidence

ORD record: ord-92062b061abc4dddaedaccefe55a2903
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531553B2

Reaction notes

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