Phosphorus oxychloride → HCID 86722261, compound

HRID 869415Notes

Reaction equation

HRID 869415 reaction equation
O[C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[S:11][CH:12]=2)[N:5]=[C:4]2[C:16]3[C:22]([Br:23])=[C:21]([O:24][CH3:25])[CH:20]=[CH:19][C:17]=3[O:18][C:3]=12.O=P(Cl)(Cl)[Cl:28]>>[Br:23][C:22]1[C:16]2[C:4]3[C:3]([O:18][C:17]=2[CH:19]=[CH:20][C:21]=1[O:24][CH3:25])=[C:2]([Cl:28])[CH:7]=[C:6]([C:8]1[N:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[S:11][CH:12]=1)[N:5]=3

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1784882614-Hydroxyl-9-bromo-2-(2-isopropyl-thiazol-4-yl)-8-methoxy-benzofuro[3,2-b]pyridine

Product 1

HCID 86722261HCID 86722261, compoundYield 16%

Conditions

Temperature
110 °C

Procedure

A mixture of 15C (1.2 g, 2.8 mmol) in POCl3 (10 mL) was heated to 110° C. and reacted for 30 min. TLC monitored the reaction. After the reaction completed, POCl3 in the reaction mixture was evaporated. The residue was added dropwise into ice-water. The precipitated solids were collected by filtration and purified by short column chromatography to give M15 (0.2 g, 16% yield).

Workup

  1. customreacted for 30 min
  2. customthe reaction
  3. customPOCl3 in the reaction mixture was evaporated
  4. additionThe residue was added dropwise into ice-water
  5. filtrationThe precipitated solids were collected by filtration
  6. custompurified by short column chromatography
  7. customto give M15 (0.2 g, 16% yield)

Sources & evidence

ORD record
ord-8a7c47fadf3e4cd08f2db144cfaa9534
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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