Cyclopropylboronic acid → HCID 58042362, compound

HRID 2048086Notes

Reaction equation

HRID 2048086 reaction equation
[F:1][CH:2]([F:11])[O:3][C:4]1[C:5](Br)=[N:6][CH:7]=[CH:8][CH:9]=1.[CH:12]1(B(O)O)[CH2:14][CH2:13]1>>[F:1][CH:2]([F:11])[O:3][C:4]1[C:5]([CH:12]2[CH2:14][CH2:13]2)=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 2760897Cyclopropylboronic acidHCID 580424482-broMo-3-(difluoroMethoxy)pyridine

Product 1

HCID 58042362HCID 58042362, compoundYield 58%

Conditions

Temperature
95 °C

Procedure

Prepared according to Preparation 48 using 3-difluoromethoxy-2-bromopyridine (Preparation 217) and cyclopropylboronic acid. The reaction was heated to 95° C. for 18 hours before cooling to room temperature and filtering through arbocel. The filtrate was concentrated in vacuo and purified using silica gel column chromatography eluting with ethylacetate:heptane 1:5 to furnish the title compound as a colourless oil (273 mg, 58%).

Workup

  1. customPrepared
  2. temperaturebefore cooling to room temperature
  3. filtrationfiltering through arbocel
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified
  6. washeluting with ethylacetate:heptane 1:5

Sources & evidence

ORD record
ord-79a046edaf4f4bf7a1ebb93ad6927f28
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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