Dichloromethane → HCID 70974574, compound

HRID 1424552Notes

Reaction equation

HRID 1424552 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12].[F:16][C:17]1[N:22]=[C:21]([F:23])[C:20]([F:24])=[C:19](F)[C:18]=1[F:26].[F-].[Cs+].ClCCl>CN(C=O)C.[Cl-].[Na+].O>[F:23][C:21]1[C:20]([F:24])=[C:19]([C:3]#[C:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N+:11]([O-:13])=[O:12])[C:18]([F:26])=[C:17]([F:16])[N:22]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 25953Cesium fluorideHCID 69690PentafluoropyridineHCID 11333470Trimethyl((2-nitrophenyl)ethynyl)silane2×

Product 1

HCID 70974574HCID 70974574, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of Trimethyl((2-nitrophenyl)ethynyl) silane, (11c) (1.10 g, 5.02 mmol) in DMF (10 mL) was added to the mixture of pentafluoropyridine (1.08 g, 6.53 mmol) and CsF(1.10 g, 7.52 mmol) in DMF (10 mL) slowly. The reaction mixture was stirred overnight. Brine (30 mL) and dichloromethane (60 mL) were added. Organic phase was separated and washed with water (30 mL×3). Solvent was evaporated by rotary evaporation and the residue was chromatographed (Hexane, then EtOAc:Hexane =1:30) to provide the desired product in 77% yield: 1H-NMR (300 MHz, CDCl3) δ 8.24 (dd, J=7.8, 1.5 Hz, 1H), 7.85 (dd, J=7.5, 1.5 Hz, 1H), 7.73 (ddd, J=7.5, 7.5, 1.5 Hz, 1H), 7.66 (ddd, J=7.8, 7.8, 1.5 Hz, 1H); 13C-NMR (150 MHz, CDCl3) δ 149.7, 143.7 (dm, J=234.1 Hz), 142.1 (dm, J=264.7 Hz), 135.5, 133.5, 131.2, 125.3, 116.7 (t, J=16.3 Hz), 116.2, 100.9 (t, J=3.2 Hz), 79.8 (t, J=4.1 Hz); HRMS (CI+): calcd for C13H5F4N2O2 [M+H]+ 297.02872, found 297.02911; m.p. 109-110° C.

Workup

  1. customOrganic phase was separated
  2. washwashed with water (30 mL×3)
  3. customSolvent was evaporated by rotary evaporation
  4. customthe residue was chromatographed (Hexane

Sources & evidence

ORD record
ord-07c5f53076544322b7a65822815ecdfe
Source dataset
uspto-grants-2015_01
Patent number
US08927728B2

Reaction notes

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