Sodium Hydroxide → HCID 59263334, compound

HRID 425733Notes

Reaction equation

HRID 425733 reaction equation
[F:1][C:2]([F:26])([F:25])[S:3]([O:6][C:7]1[CH:8]=[CH:9][C:10]2[O:24][CH2:23][C:13]3([C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][C:14]3=[O:22])[C:11]=2[CH:12]=1)(=[O:5])=[O:4].[OH-].[Na+].Br[CH2:30][C:31]1[O:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=1>CN(C)C=O.C(OCC)(=O)C>[F:26][C:2]([F:1])([F:25])[S:3]([O:6][C:7]1[CH:8]=[CH:9][C:10]2[O:24][CH2:23][C:13]3([C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]([CH2:30][C:31]4[O:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=4)[C:14]3=[O:22])[C:11]=2[CH:12]=1)(=[O:5])=[O:4]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 59263346HCID 59263346, compound

Product 1

HCID 59263334HCID 59263334, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2′-oxo-1′,2′-dihydrospiro[1-benzofuran-3,3′-indol]-5-yl trifluoromethanesulfonate (0.42 g, 1.10 mmol) and sodium hydroxide (0.07 g, 1.65 mmol) in N,N-dimethylformamide (5.00 mL) was added 2-(bromomethyl)-5-(trifluoromethyl)furan (0.50 g, 2.20 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 16 h and diluted with ethyl acetate (200 mL). After washing with aqueous saturated sodium chloride (2×20.0 mL), the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was subjected to column chromatography (ethyl acetate/hexane, ⅓) to give the title compound (0.47 g, 80%) as a clear oil: 1H NMR (300 MHz, CDCl3) δ 7.34 (t, 1H), 7.18-6.94 (m, 5H), 6.74 (dd, 1H), 6.55 (dd, 1H), 6.40 (d, 1H), 5.09-4.72 (m, 4H); MS (ES+) m/z 534.4 (M+1).

Workup

  1. washAfter washing with aqueous saturated sodium chloride (2×20.0 mL)
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b2ac5ac66dab4dad85fe1420fece760b
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

Loading…