Triethylamine → [4-(trifluoromethyl)phenyl]methyl N-(1H-indol-4-yl)carbamate

HRID 585953Notes

Reaction equation

HRID 585953 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1.[N:13]([C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH:18]=[CH:19][NH:20]2)=[C:14]=[O:15].C(N(CC)CC)C>C1COCC1>[NH:20]1[C:21]2[C:17](=[C:16]([NH:13][C:14](=[O:15])[O:10][CH2:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:11])([F:12])[F:1])=[CH:8][CH:7]=3)[CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676844-(Trifluoromethyl)benzenemethanolHCID 220326444-isocyanato-1H-indole

Product 1

HCID 11724418[4-(trifluoromethyl)phenyl]methyl N-(1H-indol-4-yl)carbamateYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[4-(Trifluoromethyl)phenyl]methanol (0.09 g, 0.55 mmol) and the product of Example 80A (0.08 g, 0.5 mmol) in THF (5 mL) were heated at reflux for 16 hours with a catalytic amount of triethylamine. The reaction mixture was concentrated under reduced pressure and the residue was purified by chromatography on silica gel eluting with 50% hexane:ethylacetate to provide the title compound as an oil (0.09 g). 1H NMR (300 MHz, DMSO-d6) δ 5.32 (s, 2H), 6.73 (s, 1H), 7.0 (t, 1H), 7.11 (d, 1H), 7.23 (t, 1H), 7.38 (d, 1H), 7.66 (d, 2H), 7.78 (d, 2H), 9.52 (s, 1H), 11.08 (s, 1H). Anal. Calcd. for C17H13N2F3O2: C, 61.08; H, 3.92; N, 8.38. Found: C, 60.97; H, 4.21; N, 8.17.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel eluting with 50% hexane

Sources & evidence

ORD record
ord-321740d0e141406d914ab7e40867b183
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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