Allyl bromide → HCID 66654496, compound

HRID 2036223Notes

Reaction equation

HRID 2036223 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:22])[C:17]=2[Br:21])[CH:12]1[C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[OH:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:37](Br)[CH:38]=[CH2:39]>CC(C)=O.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:22])[C:17]=2[Br:21])[CH:12]1[C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[O:30][CH2:39][CH:38]=[CH2:37])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 86682584HCID 86682584, compound

Product 1

HCID 66654496HCID 66654496, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of (±)-5-bromo-1-(5-chloro-2-hydroxy-phenyl)-6-fluoro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (150 mg, 0.28 mmol, 1.00 eq.) and K2CO3 (43 mg, 0.31 mmol, 1.10 eq.) in acetone (0.7 mL), allyl bromide (26 μL, 0.29 mmol, 1.05 eq.) was added. The mixture was heated to 60° C. in a sealed vial for 18 hours. The reaction mixture was allowed to cool to r.t. and poured in water (4 mL). The mixture was extracted with DCM (2×5 mL). The comb. org. phases were dried over MgSO4, filtered, and concentrated in vacuo. The residue was partially purified by flash master (column: 10 g, flow: 15 mL/min, Heptane to Heptane+10% AcOEt) to yield (±)-1-(2-allyloxy-5-chloro-phenyl)-5-bromo-6-fluoro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester as a colorless oil.

Workup

  1. additionwas added
  2. temperatureto cool to r.t.
  3. extractionThe mixture was extracted with DCM (2×5 mL)
  4. dry with materialphases were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was partially purified by flash master (column: 10 g, flow: 15 mL/min, Heptane to Heptane+10% AcOEt)

Sources & evidence

ORD record
ord-13df208ebb22409d8a08195bc3494a87
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

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