HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 491687
Notes
Print preview

Reaction equation

HRID 491687 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7638MonobenzoneHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 12210277Triethylamine; trifluoroacetic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent

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

  1. temperatureThe mixture was cooled to RT
  2. additionwas added
  3. customthe mixture was evaporated to dryness onto the silica
  4. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes