Sodium bis(trimethylsilyl)amide → HCID 118415188, compound

HRID 1507608Notes

Reaction equation

HRID 1507608 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][C:9](=[O:13])[C:10]([CH3:12])([CH3:11])[C:5]2=[CH:4][CH:3]=1.[CH:14]1(B(O)O)[CH2:16][CH2:15]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH:14]3[CH2:16][CH2:15]3)[C:9](=[O:13])[C:10]([CH3:11])([CH3:12])[C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 2760897Cyclopropylboronic acidHCID 90047413HCID 90047413, compound

Product 1

HCID 118415188HCID 118415188, compound

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a suspension of 6-chloro-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (150 mg, 763 mol), cyclopropylboronic acid (131 mg, 1.53 mmol), copper (II) acetate (145 mg, 801 μmol) and DMAP (280 mg, 2.29 mmol) in toluene (15 ml) was added sodium bis(trimethylsilyl)amide (2 M in THF, 400 μl, 801 μmol). While bubbling dry air through the reaction mixture, it was heated to 95° C. and stirred for 16 hours. The reaction mixture was poured into 1 M aqueous HCl solution (20 ml) and extracted with tBuOMe. The organic layers were washed with 1 M aqueous HCl solution and brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by silica gel chromatography using heptane/ethyl acetate as eluent. The title compound was obtained as yellow viscous oil (178 mg).

Workup

  1. customWhile bubbling
  2. customdry air through the reaction mixture, it
  3. additionThe reaction mixture was poured into 1 M aqueous HCl solution (20 ml)
  4. extractionextracted with tBuOMe
  5. washThe organic layers were washed with 1 M aqueous HCl solution and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-062a1d2594b14fab84356cd5923a6c78
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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