Allyl bromide → HCID 22218226, compound

HRID 1795604Notes

Reaction equation

HRID 1795604 reaction equation
[C:1]([C:5]1[C:14]2[CH:13]=[C:12]([NH:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=3)[CH:11]=[CH:10][C:9]=2[C:8]([CH3:28])([CH3:27])[CH2:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:35](Br)[CH:36]=[CH2:37].CC(N(C)C)=O>CCOCC>[C:1]([C:5]1[C:14]2[CH:13]=[C:12]([N:15]([CH2:37][CH:36]=[CH2:35])[C:16]3[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=3)[CH:11]=[CH:10][C:9]=2[C:8]([CH3:27])([CH3:28])[CH2:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 22218281HCID 22218281, compound2×

Product 1

HCID 22218226HCID 22218226, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of ethyl 4-(8-t-butyl-5,5-dimethyl-5,6-dihydronaphthalen-2-ylamino)-benzoate (Compound 84, 170 mg, 0.45 mmol), K2CO3 (900 mg), allyl bromide (1 mL) and dimethylacetamide (5 mL) was heated to 75° C. in a sealed tube for 7 days. The mixture was diluted with ether (70 mL), washed with brine, dried and the solvent was removed. Silica gel flash chromatography gave the title compound.

Workup

  1. washwashed with brine
  2. customdried
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-088e0dff51a448ba92a31da744a6bb3d
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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