Toluene → HCID 66876371, compound

HRID 1666380Notes

Reaction equation

HRID 1666380 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[N:6][CH:7]=1.[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].C1(C)C=CC=CC=1>ClCCl>[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:28]=[CH:27][CH:26]=[C:11]([CH:12]=[C:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 86623899tert-Butyl 4-(3-(5-bromopyrimidin-2-yloxy)benzylidene)piperidine-1-carboxylate

Product 1

HCID 66876371HCID 66876371, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(3-(5-bromopyrimidin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.285 g, 0.629 mmol) was suspended in dichloromethane (4 mL) and treated with trifluoroacetic acid (2 mL). The reaction mixture was stirred at ambient temperature for 3 h. Toluene was added and the reaction was concentrated in vacuo. After evaporating again from toluene, the residue was dried in vacuo to afford the title compound (0.385 g, quantitative yield based on 2.3 eq trifluoroacetic acid) as an orange oil. This material was dissolved in acetonitrile (3 mL) and used in the next step.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customAfter evaporating again from toluene
  3. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-e642740779d24075a82c6f5833d4979b
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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