Sodium bis(trimethylsilyl)amide → HCID 178467403, compound

HRID 1802455Notes

Reaction equation

HRID 1802455 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]1[C:23]([O:24][CH2:25][CH3:26])=[N:22][CH:21]=[CH:20][C:10]=1[C:11]([N:13](C(C)C)C(C)C)=[O:12].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:13]=[C:11]([OH:12])[C:10]3[C:9]([C:3]=2[CH:4]=1)=[C:23]([O:24][CH2:25][CH3:26])[N:22]=[CH:21][CH:20]=3

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amide2×HCID 59436003HCID 59436003, compound

Product 1

HCID 178467403HCID 178467403, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-amino-5-bromophenyl)-2-ethoxy-N,N-diisopropylisonicotinamide (17.9 g, 43 mmol) in THF (213 mL) at 0° C. was added sodium bis(trimethylsilyl) amide (1.0 M in THF, 85 mL, 85 mmol). The solution was stirred for 2 hr and monitored by LCMS. Another 10 mL of sodium bis(trimethylsilyl) amide was added and stirred for an additional 30 min. The solution was quenched with methanol and concentrated to a slurry which was subsequently triturated with water and filtered to provide the title compound.

Workup

  1. stirringstirred for an additional 30 min
  2. customThe solution was quenched with methanol
  3. concentrationconcentrated to a slurry which
  4. customwas subsequently triturated with water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-98ceb9dea65e4d6d9fdebeed094cfd64
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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