1-Bromopropane → HCID 10298436, compound

HRID 2253345Notes

Reaction equation

HRID 2253345 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:27]2[N:31]([CH3:32])[CH:30]=[N:29][CH:28]=2)[O:10][CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2[C:20]2[CH:25]=[CH:24][C:23](=[O:26])[NH:22][CH:21]=2)=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].[CH3:35][CH2:36][CH2:37]Br>CN(C=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:27]2[N:31]([CH3:32])[CH:30]=[N:29][CH:28]=2)[O:10][CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2[C:20]2[CH:25]=[CH:24][C:23](=[O:26])[N:22]([CH2:35][CH2:36][CH3:37])[CH:21]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 17966015HCID 17966015, compound

Product 1

HCID 10298436HCID 10298436, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 91F (27.3 mg, 0.0648 mmol) in DMF (2 mL) at 0° C. was treated with NaH (60%, 3.1 mg, 0.0777 mmol), stirred for 15 minutes, and treated with n-propyl bromide (11.8 μL, 0.130 mmol). The mixture was slowly warmed to room temperature and stirred for about 18 hours. The mixture was quenched with saturated NH4Cl and extracted with ethyl acetate. The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography with 10:0.2:0.02 to 10:1:0.1 ethyl acetate/methanol/NH4OH to provide 10.5 mg (35%) of the desired product. MS (HR-FAB) m/z calculated: 464.2087 (M+H)+; observed: 464.2078 (M+H)+; 1H NMR (CDCl3) δ: 7.67 (d, 1H), 7.59 (d, 1H), 7.53 (d, 1H), 7.47-7.44 (m, 3H), 7.26-7.24 (m, 3H), 6.96 (s, 1H), 6.60-6.58 (m, 1H), 5.58 (s, 1H), 4.50 (q, 2H), 3.86 (t, 2H), 3.33 (s, 3H), 1.80-1.74 (m, 2H), 0.94 (t, 3H).

Workup

  1. stirringstirred for about 18 hours
  2. customThe mixture was quenched with saturated NH4Cl
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography with 10:0.2:0.02 to 10:1:0.1 ethyl acetate/methanol/NH4OH

Sources & evidence

ORD record
ord-45f534db15bb477c9236bf06dbff74b8
Source dataset
uspto-grants-2008_01
Patent number
US07323570B2

Reaction notes

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