Dichloromethane → HCID 67006385, compound

HRID 564333Notes

Reaction equation

HRID 564333 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]23[C:24]4[C:19](=[C:20]([F:26])[CH:21]=[CH:22][C:23]=4[F:25])[O:18][CH2:17][CH:16]2[NH:15][CH2:14][CH2:13][CH2:12]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:34]CCl>>[Cl:34][C:22]1[C:23]([F:25])=[C:24]2[C:19](=[C:20]([F:26])[CH:21]=1)[O:18][CH2:17][CH:16]1[C:11]2([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:9])=[O:10])[CH2:12][CH2:13][CH2:14][NH:15]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 670064054a-(4-Chloro-benzenesulfonyl)-5,8-difluoro-2,3,4,4a,10,10a-hexahydro-1H-9-oxa-1-aza-phenanthrene

Product 1

HCID 67006385HCID 67006385, compound

Conditions

Temperature
0 °C

Procedure

4a-(4-Chloro-benzenesulfonyl)-5,8-difluoro-2,3,4,4a,10,10a-hexahydro-1H-9-oxa-1-aza-phenanthrene (1.0190 g, 2.5475 mmol) was dissolved in 75 ml dichloromethane and cooled to 0° C. then triethylamine (1.1 mL) was added. The solution was stirred at 0° C. for 10 minutes then II was added slowly and the solution was stirred at 0° C. for 3 h. Then the reaction was warmed to room temperature and stirred for 1 h. The reaction was quenched with 50 ml of ice water. The organic layer washed with 50 ml of 1 N HCl solution and dried over sodium sulfate. The product was purified by column using EtOAc/Hex. as the eluent (gradient from 0/100 to 50/50 in 45 minutes). Yield: 124.0 mg, 11%. 1H NMR (CDCl3 400 MHz) δ 7.57 (d, J=8.8 Hz, 2H), 7.52 (d, J=8.8 Hz, 2H), 7.23 (dd, J=9.5, 6.6 Hz, 1H), 5.19 (dd, J=8.8, 6.6 Hz, 1H), 4.32 (d, J=11.7 Hz, 1H), 3.69 (s, 1H), 2.99 (d, J=13.1 Hz, 1H), 2.74 (td, J=13.1, 2.9 Hz, 1H), 2.64 (d, J=13.1 Hz, 1H), 2.20-2.11 (m, 1H), 1.62 (d, J=13.1 Hz, 2H), 1.19-1.06 (m, 1H).

Workup

  1. stirringthe solution was stirred at 0° C. for 3 h
  2. temperatureThen the reaction was warmed to room temperature
  3. stirringstirred for 1 h
  4. customThe reaction was quenched with 50 ml of ice water
  5. washThe organic layer washed with 50 ml of 1 N HCl solution
  6. dry with materialdried over sodium sulfate
  7. customThe product was purified by column
  8. customas the eluent (gradient from 0/100 to 50/50 in 45 minutes)

Sources & evidence

ORD record
ord-c6e104d329584362813afe5712eaa968
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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