Phenylphosphonic dichloride → HCID 86677087, compound

HRID 1520395Notes

Reaction equation

HRID 1520395 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[N:15]=[C:16]3O)=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C1(P(Cl)([Cl:34])=O)C=CC=CC=1>>[Cl:34][C:16]1[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:18]=2)[CH:13]=[C:14]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[N:15]=1

Participants

3

Reactant 2

HCID 69990Phenylphosphonic dichlorideHCID 178489660HCID 178489660, compound

Product 1

HCID 86677087HCID 86677087, compound

Conditions

Temperature
120 °C

Procedure

To a mixture of 7-(3-methoxyphenyl)-3-(pyridin-3-yl)isoquinolin-1-ol (130 mg, 0.395 mmol) in phenylphosphonic dichloride (5 mL) was stirred at 120° C. overnight. After the reaction was completed, the mixture was added to ice-water slowly. The pH was adjusted to 7 by slow addition of NH3H2O at 0° C. Then the mixture was extracted with dichloromethane (100 mL×3). The combined organic layer were dried over MgSO4, filtered and concentrated in vacuo to give 130 mg of crude lxix-a as a white solid, which was used directly in the next step without purification. LCMS m/z=346.9 (M+1) (Method B) (retention time=1.80 min).

Workup

  1. additionThe pH was adjusted to 7 by slow addition of NH3H2O at 0° C
  2. extractionThen the mixture was extracted with dichloromethane (100 mL×3)
  3. dry with materialThe combined organic layer were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give 130 mg of crude lxix-a as a white solid, which
  7. customwas used directly in the next step without purification

Sources & evidence

ORD record
ord-7e332a314be242cda497664a3d26f609
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

Loading…