Sodium Bicarbonate → HCID 123735747, compound

HRID 2202718Notes

Reaction equation

HRID 2202718 reaction equation
Cl.[Cl:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[C:5]([Cl:10])[C:4]=1[CH:11]([O:14][Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17])[CH2:12][NH2:13].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[C:5]([Cl:10])[C:4]=1[CH:11]([O:14][Si:15]([CH2:16][CH3:17])([CH2:20][CH3:21])[CH2:18][CH3:19])[CH2:12][NH2:13]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 131735769HCID 131735769, compound

Product 1

HCID 123735747HCID 123735747, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 mL three-necked RBF were added (1-(2,6-dichloro-3-fluorophenyl)-2-nitroethoxy)triethylsilane (3.64 g, 9.88 mmol) in EtOH (16 ml) and water (4 ml) at room temperature followed by addition of iron (5.52 g, 99 mmol) and ammonium chloride (5.29 g, 99 mmol). The flask was purged with nitrogen and was heated to 60° C. under nitrogen for 3 h. The mixture was cooled to room temperature, diluted with 40 mL of MeOH, sonicated for 10 min. Then the solution was decanted through a pad of celite. This process was repeated for three times. The filtrate was concentrated to ˜30 mL and diluted with EtOAc (120 mL). The solid was filtered off and discarded. The filtrate was concentrated under reduced pressure. It was diluted with 50 mL of EtOAc, washed with water, brine, dried over anhydrous MgSO4, and concentrated to give 2-(2,6-dichloro-3-fluorophenyl)-2-((triethylsilyl)oxy)ethanamine hydrochloride as an off-white solid. The HCl salt was dissolved with 50 mL of DCM. The suspension was basicified w/satd aq NaHCO3 (pH=9). The organic layer was separated, washed with brine, dried over anhydrous MgSO4, and concentrated to give 2-(2,6-dichloro-3-fluorophenyl)-2-((triethylsilyl)oxy)ethanamine (2.73 g, 8.07 mmol, 82% yield) as a brown oil. 1H NMR (400 MHz, CDCl3) δ 7.23-7.29 (m, 1H), 6.99-7.06 (m, 1H), 5.35 (dd, J=8.6, 4.9 Hz, 1H), 3.29 (dd, J=13.1, 8.7 Hz, 1H), 2.92 (dd, J=13.2, 4.9 Hz, 1H), 0.83-0.93 (m, 9H), 0.46-0.61 (m, 6H); LCMS: 338.2 [M+H]+.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bdfa0f2fe5434a00939e48d5eb933f13
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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