Sodium bis(trimethylsilyl)amide → HCID 178450360, compound

HRID 2192960Notes

Reaction equation

HRID 2192960 reaction equation
N[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:3]=1[C:13]1[CH:27]=[C:26]([Br:28])[CH:25]=[CH:24][C:14]=1[C:15]([N:17](C(C)C)C(C)C)=[O:16].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[Br:28][C:26]1[CH:25]=[CH:24][C:14]2[C:15]([OH:16])=[N:17][C:2]3[C:3]([C:13]=2[CH:27]=1)=[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH3:12])[N:5]=[CH:6][CH:7]=3

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 593755822-(4-Amino-2-butoxypyridin-3-yl)-4-bromo-N,N-di(propan-2-yl)benzamide

Product 1

HCID 178450360HCID 178450360, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-amino-2-butoxypyridin-3-yl)-4-bromo-N,N-diisopropylbenzamide (8.5 g, 19.0 mmol) in THF (135 mL) was added sodium bis(trimethylsilyl)amide (38 mL, 38 mmol, 1.0 M in THF) dropwise at 0° C. under nitrogen. The solution was allowed to stir for 2 hr then quenched with water. The solid precipitate was filtered, collected, and dried under vacuum to afford 9-bromo-1-butoxybenzo[c]-1,6-naphthyridin-6-ol as a white solid. 1H NMR (600 MHz, CD6SO) δ 9.22 (s, 1H), 8.2 (d, 1H), 8.05 (d, 1H), 7.78 (d, 1H), 6.92, (d, 1H), 4.45 (t, 2H), 1.86 (m, 2H), 1.59 (m, 21-1), 1.0 (t, 3H). LRMS (ESI) calc'd for (C16H15BrN2O2) [M+H]+, 347.0; found 347.0.

Workup

  1. customthen quenched with water
  2. filtrationThe solid precipitate was filtered
  3. customcollected
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e15e71c98d1741738e6d6e81c534a038
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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