Pyridine → HCID 86614617, compound

HRID 1047519Notes

Reaction equation

HRID 1047519 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]23[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH:12]2[CH2:13][O:14][C:15]2[C:20]3=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:28](Cl)([Cl:30])=[O:29].N1C=CC=CC=1>C(Cl)Cl>[Cl:30][C:28]([O:27][CH:24]1[CH2:23][CH:12]2[CH2:13][O:14][C:15]3[C:20]([C:11]2([S:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)(=[O:10])=[O:9])[CH2:26][CH2:25]1)=[C:19]([F:21])[CH:18]=[CH:17][C:16]=3[F:22])=[O:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 46884866HCID 46884866, compound

Product 1

HCID 86614617HCID 86614617, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10a-(4-chloro-benzenesulfonyl)-1,4-difluoro-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-8-ol (0.46 g, 1.11 mmole) was dissolved in 30 ml DCM. Phosgene (20% in toluene, 4 ml) and pyridine (1 ml) were added and the reaction was stirred at room temperature for 10 minutes. 20 ml DCM was added and the reaction was quenched by slowly adding 10 ml water. The organic layer was washed with 50 ml 1N HCl solution, dried over sodium sulfate. After the solvent was removed, the residue was purified by column using EtOAc/Hex. as the solvent (gradient from 0/100 to 25/75 in 25 minutes). Yield: 0.37 g, 70%. 1H NMR (CDCl3 400 MHz) δ 7.62 (d, 2H, J=8.8 Hz), 7.50 (d, 2H, J=8.8 Hz), 7.06-7.13 (m, 1H), 6.40-6.47 (m, 1H), 5.28 (dd, 1H, J=11.7 and 2.9 Hz), 5.05 (s, 1H,), 4.14 (d, 1H, J=11.7 Hz), 3.02 (dt, J=13.2 and 2.9 Hz, 1H), 2.31-2.49 (m, 2H), 2.01-2.16 (m, 2H), 1.66-1.75 (m, 1H), 1.30-1.40 (m, 1H).

Workup

  1. customthe reaction was quenched
  2. additionby slowly adding 10 ml water
  3. washThe organic layer was washed with 50 ml 1N HCl solution
  4. dry with materialdried over sodium sulfate
  5. customAfter the solvent was removed
  6. customthe residue was purified by column
  7. customas the solvent (gradient from 0/100 to 25/75 in 25 minutes)

Sources & evidence

ORD record
ord-bfae1f09305a4acbba31ec6ce60411f5
Source dataset
uspto-grants-2013_10
Patent number
US08569521B2

Reaction notes

Loading…