Cesium carbonate → HCID 11223760, compound

HRID 2373905Notes

Reaction equation

HRID 2373905 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:18]3[CH2:21][CH2:20][CH2:19]3)=[N:9][C:10]=2[C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][N:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[N+:28]([C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33]Br)([O-:30])=[O:29]>CN(C=O)C>[CH:18]1([C:8]2[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]3=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:33][C:32]4[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=4[N+:28]([O-:30])=[O:29])[CH:12]=3)[N:9]=2)[CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 77569alpha-Bromo-2-nitrotolueneHCID 11716093HCID 11716093, compound

Product 1

HCID 11223760HCID 11223760, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-(8-Amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenol (2.00 g, 7.13 mmol) in DMF (36.7 mL) was charged with Cs2CO3 (3.48 g, 10.7 mmol) and stirred at rt for 30 min. A DMF solution of 2-nitrobenzyl bromide (1.54 g, 7.13 mmol), was then added to the reaction mixture. The reaction was allowed to progress at rt under nitrogen for 3.5 h. TLC analysis showed that the reaction was complete. The product was purified using silica gel column chromatography (1-3% NH3 in MeOH:CH2Cl2). The final product was concentrated to a yellow solid; 1H NMR (CDCl3, 400 MHz) δ 2.00-2.08 (m, 1H), 2.11-2.23 (m, 1H), 2.45-2.53 (m, 2H), 2.59-2.69 (m, 2H), 3.77-3.86 (m, 1H), 5.57 (s, 2H), 7.01-7.05 (m, 2H), 7.11 (d, J=5.6 HZ, 1H), 7.27-7.30 (m, 1H), 7.32-7.33 (m, 1H), 7.42 (t, J=16.4 Hz, 1H), 7.48-7.52 (m, 1H), 7.67-7.71 (m, 1H), 7.92 (dd, J=8.0 Hz, 1H), 8.17 (d, J=9.5 Hz, 1H); MS (ES+): m/z 416.01 (100) [MH+].

Workup

  1. waitto progress at rt under nitrogen for 3.5 h
  2. customThe product was purified
  3. concentrationThe final product was concentrated to a yellow solid

Sources & evidence

ORD record
ord-575dbb2a4ec64750b84b698de7ad48d7
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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