Bromocyclopropane → HCID 86683274, compound

HRID 1852265Notes

Reaction equation

HRID 1852265 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[C:5]([OH:13])=[CH:4][N:3]=1.[CH2:14]1CCN2C(=NCCC2)C[CH2:15]1.C1(Br)CC1>O>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[C:5]([O:13][CH2:14][CH3:15])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 78037BromocyclopropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86683273HCID 86683273, compound

Product 1

HCID 86683274HCID 86683274, compoundYield 2.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1,5-dichloroisoquinolin-4-ol (0.5 g, 2.33 mmol) in DBU (1.7 ml, 11.68 mmol) was added cyclopropylbromide (0.93 ml, 11.68 mmol) at room temperature. The reaction vessel (Pressure tube) was sealed and heated at 120° C. for 18 h. The reaction mass was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (0.01 g, 2.1%) as yellow solid. 1H NMR (400 MHz, CDCl3): δ ppm 8.27-8.24 (m, 2H), 7.76-7.74 (d, J=8 Hz, 1H), 7.54 (t, J=8 Hz, 1H), 3.96-3.94 (m, 1H), 0.95-0.90 (m, 4H).

Workup

  1. customThe reaction vessel (Pressure tube) was sealed
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. customevaporated under reduced pressure
  5. customto get crude compound
  6. customThe crude compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c79727c5e5f046228af72ad5616a2679
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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