2,6-Lutidine → HCID 58065847, compound

HRID 508233Notes

Reaction equation

HRID 508233 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][C:17](=O)[CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.N1C(C)=CC=CC=1C.Cl.[CH2:36]([O:43][NH2:44])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1COCC1>[CH2:36]([O:43]/[N:44]=[C:17](\[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)/[CH2:16][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([Br:15])=[CH:11][C:12]=2[C:13]2[C:5]1=[CH:4][CH:3]=[C:2]([Br:1])[CH:14]=2)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 102312Benzyloxyamine hydrochlorideHCID 58065823HCID 58065823, compound

Product 1

HCID 58065847HCID 58065847, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step 1 (17.7 mg, 0.0374 mmol, 1.0 equiv) in THF (400 μL) were added 2,6-lutidine (4.4 μL, 0.0374 mmol, 1.0 equiv), O-benzylhydroxylamine hydrochloride (14.3 mg, 0.0898 mmol, 2.4 equiv) and 4A molecular sieves (15.8 mg). The mixture was stirred for 12 h until TLC indicated complete consumption of starting material. The reaction mixture was quenched with saturated NaHCO3 and extracted 3 times with dichloromethane. The combined organic extracts were dried with MgSO4 and concentrated to give crude product. It was further purified by silica gel chromatography (5-10% EtOAc/Hex) to afford 20.2 mg white solid as product, yield 93.4%. 1H NMR (CDCl3, 400 MHz) δ=4.68 (s, 2H) 5.00 (s, 2H) 5.14 (s, 2H) 6.72 (d, J=8.2 Hz, 2H) 6.94 (t, J=7.3 Hz, 1H) 7.47-7.16 (m, 11H) 8.06 (s, 2H)

Workup

  1. customconsumption of starting material
  2. customThe reaction mixture was quenched with saturated NaHCO3
  3. extractionextracted 3 times with dichloromethane
  4. dry with materialThe combined organic extracts were dried with MgSO4
  5. concentrationconcentrated
  6. customto give crude product
  7. customIt was further purified by silica gel chromatography (5-10% EtOAc/Hex)

Sources & evidence

ORD record
ord-856986b1c92345d4b9b7a63f16f03d19
Source dataset
uspto-grants-2015_08
Patent number
US09095572B2

Reaction notes

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