Methanol → HCID 72335435, compound

HRID 2264731Notes

Reaction equation

HRID 2264731 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2(C3C=CN=CC=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:18])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:25][C:26]([S:29](N)=[O:30])([CH3:28])[CH3:27].CO.C(=O)(O)[O-].[Na+]>CCO.CCO.CCO.CCO.[Ti].C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]#[N:18])=[N:10][S:29]([C:26]([CH3:28])([CH3:27])[CH3:25])=[O:30])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 3382465Tert-ButanesulfinamideHCID 59596252HCID 59596252, compound

Product 1

HCID 72335435HCID 72335435, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 2724286Titanium(IV)ethoxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(3-bromo-4-fluorobenzoyl)benzonitrile (Scheme #11, E) and tetraethyl orthotitanate (1 M solution in tetrahydrofuran, 18.3 mL, 18.3 mmol) was stirred for 5 minutes, then 2-methyl-2-propanesulfinamide (1.11 g, 9.13 mmol) was added and the resulting mixture was heated to reflux over night. When the reaction had cooled to room temperature methanol, aqueous saturated sodium bicarbonate and ethyl acetate was added. After filtering the reaction mixture through a pad of sodium sulfate, the filtrate was concentrated. Purification of the residue by column chromatography using chloroform as the eluent gave the title compound (1.22 g, 30% over 2 steps). 1H NMR (CDCl3) δ 7.90-7.69 (m, 3 H), 7.68-7.39 (m, 3 H), 7.18 (t, J=8.21 Hz, 1 H), 1.38 (br s, 9 H); MS (AP) m/z 407, 409 [M+1]+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux over night
  3. additionwas added
  4. filtrationAfter filtering the reaction mixture through a pad of sodium sulfate
  5. concentrationthe filtrate was concentrated
  6. customPurification of the residue by column chromatography

Sources & evidence

ORD record
ord-351697bbac184ac18dc2f3aefa693b2a
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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