Sodium hydride → HCID 87826036, compound

HRID 1594510Notes

Reaction equation

HRID 1594510 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([S:15]([CH2:18]C)(=[O:17])=[O:16])=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:5]=2[N:4]=[C:3]1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1.[H-].[Na+].[CH3:34][O:35][C:36](=[O:45])[C:37]1[CH:42]=[CH:41][C:40]([CH2:43]Br)=[CH:39][CH:38]=1>CN(C=O)C.C(Cl)Cl.C([O-])(O)=O.[Na+].[Cl-].[Na+].O>[CH3:1][N:2]1[C:6]2[C:7]([S:15]([CH3:18])(=[O:16])=[O:17])=[CH:8][C:9]([C:11]([F:13])([F:12])[F:14])=[CH:10][C:5]=2[N:4]([CH2:43][C:40]2[CH:41]=[CH:42][C:37]([C:36]([O:35][CH3:34])=[O:45])=[CH:38][CH:39]=2)[C:3]1=[N:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:29])([F:31])[F:30])=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 87690289HCID 87690289, compound

Product 1

HCID 87826036HCID 87826036, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 129703874Sodium hydrogencarbonate brineSolvent

Procedure

A flask containing the title compound from Example 10, Step A (30 mg, 0.066 mmol) was charged with sodium hydride (60% suspension in mineral oil, 4.0 mg, 0.10 mmol), and the mixture was dissolved in DMF (1.5 mL). After ten minutes, methyl4-(bromomethyl)benzoate (18 mg, 0.077 mmol) was added and the mixture was stirred at room temperature. After 15 h, the mixture was diluted with CH2Cl2 and poured in saturated aq. NaHCO3/brine. The phases were separated, and the organic phase was dried over Na2SO4 and concentrated. The crude reaction mixture, containing both N-benzyl regioisomers, was taken forward directly: LC-MS (ESI, Method B) 2.25 min, m/z 602.3 (M+1).

Workup

  1. waitAfter ten minutes
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude reaction mixture
  6. additioncontaining both N-benzyl regioisomers
  7. customLC-MS (ESI, Method B) 2.25 min, m/z 602.3 (M+1)

Sources & evidence

ORD record
ord-6ece8340aab54adc8cd33e20f2fded58
Source dataset
uspto-grants-2007_11
Patent number
US07301036B2

Reaction notes

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