Water → HCID 77230757, compound

HRID 1521612Notes

Reaction equation

HRID 1521612 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:11](OC)=[O:12])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C.O.S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:11][OH:12])[CH2:9][CH2:10]2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21225700DiisobutylaluminumhydrideHCID 59578399Methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate

Product 1

HCID 77230757HCID 77230757, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of the title compound from Example 71 Step B (200 mg, 0.78 mmol) in tetrahydrofuran (3.9 mL) at 0° C. was added a solution of diisobutyl aluminum hydride in hexanes (1.0 M, 1.56 mL, 1.56 mmol). The reaction was warmed to room temperature and stirred overnight. Water and magnesium sulfate were then added, and the resulting suspension was stirred for 30 minutes, then filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel (20-100% ethyl acetate in hexanes) provided the title compound: LCMS m/z 229.67 [M+2+H]+; 1H NMR (500 MHz, CDCl3) δ 8.50 (s, 2H), 7.83 (s, 1H), 3.69 (s, 2H), 0.96-0.90 (m, 4H).

Workup

  1. stirringthe resulting suspension was stirred for 30 minutes
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography on silica gel (20-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f6484419ed9a4fffa752cc5b487a0782
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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