Formaldehyde → HCID 69331104, compound

HRID 585151Notes

Reaction equation

HRID 585151 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([C@@:8]2([F:22])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:21])[CH:7]=1.[C:25]([O-])([O-])=[O:26].[K+].[K+].C=O.O>C1COCC1.C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([C@@:8]2([F:22])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[N:10]([CH2:25][OH:26])[C:9]2=[O:21])[CH:7]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 214350Bms 204352

Product 1

HCID 69331104HCID 69331104, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (S)-3-(5-chloro-2-methoxy-phenyl)-3-fluoro-6-trifluoromethyl-1,3-dihydro-indol-2-one ((S)-II) (60.0 g, 0.167 mol) and K2CO3 (27.7 g, 0.20 mol) in THF (600 mL) was added formaldehyde (37% solution in H2O, 240 mL, 3.2 mol) followed by H2O (300 mL). The lightly turbid mixture was stirred at room temperature for 3 hours, and diluted with diethyl ether (1000 mL). The organic layer was separated. The aqueous layer was washed with ether (200 mL×2). The combined organic layer was washed with brine, dried over Na2SO4. Evaporation of solvents provided the title compound as a white dry foam (64.5 g, 99% yield). LC/MS m/e: 390 (MH+), 96% purity. 1H NMR (CDCl3): δ 3.50 (s, 3H), 5.28 (m, 1H), 5.45 (m, 1H), 6.75 (dd, J=1.5, 6.5 Hz, 1H), 7.24 (m, 1H), 7.34 (m, (m, 3H), 7.79 (dd, J=1.0, 3.0 Hz, 1H).

Workup

  1. customThe organic layer was separated
  2. washThe aqueous layer was washed with ether (200 mL×2)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation of solvents

Sources & evidence

ORD record
ord-c8c2ef5c8e6e4bc280f0dfa1b0277a3c
Source dataset
uspto-grants-2005_08
Patent number
US06930100B2

Reaction notes

Loading…