Dichloromethane → HCID 11580240, compound

HRID 724731Notes

Reaction equation

HRID 724731 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1B(O)O.[C:12]([N:16]1[C:20](=[O:21])[CH:19]=[C:18](Cl)[S:17]1(=[O:24])=[O:23])([CH3:15])([CH3:14])[CH3:13].ClCCl.C(N(CC)CC)C>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:12]([N:16]1[C:20](=[O:21])[CH:19]=[C:18]([C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[F:1])[S:17]1(=[O:23])=[O:24])([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 2783132(2-Fluoro-4-methylphenyl)boronic acidHCID 218786382-Tert-butyl-5-chloro-2,3-dihydro-1lambda6,2-thiazole-1,1,3-trione

Product 1

HCID 11580240HCID 11580240, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

(2-Fluoro-4-methylphenyl)boronic acid (19.5 g, 0.127 mol), 2-tert-butyl-5-chloro-1,1-dioxo-1,2-dihydro-1λ6-isothiazol-3-one (30.5 g, 0.136 mol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (10.4 g, 12.7 mmol) were dissolved in toluene (500 mL) and treated with triethylamine (53.0 mL, 0.380 mol). The reaction was degassed and placed under an atmosphere of nitrogen. The reaction was then heated to 90° C. for 18 h. The reaction was diluted with ethyl acetate (500 mL) and washed with 1 N aqueous hydrochloric acid (500 mL). The ethyl acetate was dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was filtered through celite and then silica gel. The crude material was then purified by silica gel chromatography (5–10% ethyl acetate:hexanes) to afford product as a white solid (24.5 g, 65%). 1H NMR (400 MHz, CDCl3): δ 7.85 (t, J=7.8 Hz, 1H), 7.11–7.03 (m2H), 6.86 (d, J=1.8 Hz, 1H), 2.42 (s, 3H), 1.73 (s, 9H).

Workup

  1. customThe reaction was degassed
  2. additionThe reaction was diluted with ethyl acetate (500 mL)
  3. washwashed with 1 N aqueous hydrochloric acid (500 mL)
  4. dry with materialThe ethyl acetate was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationThe crude material was filtered through celite
  8. customThe crude material was then purified by silica gel chromatography (5–10% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-ff3b95ac26c848afa28434cc5896ea04
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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