Lithium Hexamethyldisilazide → HCID 57489640, compound

HRID 2044092Notes

Reaction equation

HRID 2044092 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl[C:12]1[N:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:13]=1[C:14]([NH2:16])=[O:15].[NH2:22][C:23]1[CH:24]=[C:25]([N:29]([CH3:39])[S:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH:26]=[CH:27][CH:28]=1>C1COCC1.CCOC(C)=O>[Cl:21][C:19]1[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=[O:15])=[C:12]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:39])[S:30]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)(=[O:32])=[O:31])[CH:24]=2)[N:20]=1

Participants

6

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 221427782,6-Dichloropyridine-3-carboxamideHCID 57489639HCID 57489639, compound

Product 1

HCID 57489640HCID 57489640, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 1 M THF solution of LiHMDS (2.302 mL, 2.302 mmol) was added dropwise to a suspension of 2,6-dichloronicotinamide (163 mg, 0.855 mmol) and N-(3-aminophenyl)-N-methylbenzenesulfonamide (172.5 mg, 0.658 mmol) in THF (3 mL) at room temperature. After 18 h at room temperature, the mixture was diluted with EtOAc and washed with saturated NH4Cl (5 mL). The EtOAc phase was concentrated and purified by silica gel chromatography, eluting with 20-100% EtOAc in hexanes, to give a yellow solid (218.8 mg, 51% yield). LCMS: (M+H)+=417.0.

Workup

  1. washwashed with saturated NH4Cl (5 mL)
  2. concentrationThe EtOAc phase was concentrated
  3. custompurified by silica gel chromatography
  4. washeluting with 20-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-d72b9bcbc0b2402b8218a84aa86a197f
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

Loading…