2-[4-(2-Nitro-vinyl)-phenoxy]-5-trifluoromethyl-pyridine → 2-(4-(5-Trifluoromethyl-2-pyridinyloxy)phenyl)ethylamine

HRID 705965Notes

Reaction equation

HRID 705965 reaction equation
[N+:1]([CH:4]=[CH:5][C:6]1[CH:22]=[CH:21][C:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=2)=[CH:8][CH:7]=1)([O-])=O>O1CCCC1>[F:19][C:17]([F:18])([F:20])[C:14]1[CH:15]=[CH:16][C:11]([O:10][C:9]2[CH:21]=[CH:22][C:6]([CH2:5][CH2:4][NH2:1])=[CH:7][CH:8]=2)=[N:12][CH:13]=1

Participants

3

Reactant 1

HCID 677734032-[4-(2-Nitro-vinyl)-phenoxy]-5-trifluoromethyl-pyridine

Product 1

HCID 167707892-(4-(5-Trifluoromethyl-2-pyridinyloxy)phenyl)ethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Entire reaction was performed under argon atmosphere using syringe septa technique. To a stirred suspension of LiA1H4 (3.062 mmol, 2.5 eq) in dry tetrahydrofurane (20 ml) was added 2-[4-(2-nitro-vinyl)-phenoxy]-5-trifluoromethyl-pyridine (1.225 mmol, 1 eq) dissolved in dry tetrahydrofurane (10 ml) dropwise. Reaction mixture was stirred at rt for 2 h. Reaction mixture was quenched with 0.5 ml water. Celite and NaOH (3 ml, 5 N) were added and the mixture was filtered through Celite, rinsing the filter cake well with ether and DCM. Solvents were evaporated till dry. Crude product was purified on Biotage SP1 Snap Si 25; 25 ml/min in the gradient of MeOH in DCM: 0-5% for 3CV then from 5-40% for 30 CV. The appropriate fractions were combined and evaporated in vacuo to give the required product 2-[4-[5-trifluoromethyl-pyridin-2yloxy)phenyl]-ethylamine s yellow oil (0.443 mmol, yield=36%, purity=91%). [M+H]+=283.30 1H NMR (300 MHz, DMSO-d6) δ/ppm 2.68 (d, 2H), 2.79 (d, J=7.5 Hz, 2H), 7.06-7.13 (m, 2H), 7.19 (d, J=8.7 Hz, 1H), 7.23-7.29 (m, 2H), 8.17-8.20 (m, 1H), 8.20-8.23 (m, 1H), 8.51-8.57 (m, 2H)

Workup

  1. customEntire reaction
  2. customReaction mixture
  3. customReaction mixture
  4. customwas quenched with 0.5 ml water
  5. additionCelite and NaOH (3 ml, 5 N) were added
  6. filtrationthe mixture was filtered through Celite
  7. washrinsing the filter cake well with ether and DCM
  8. customSolvents were evaporated
  9. customtill dry
  10. customCrude product was purified on Biotage SP1 Snap Si 25
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-cd9ef596d4f6422e9865a2dc6e798259
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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