Butyl iodide → HCID 22559177, compound

HRID 984715Notes

Reaction equation

HRID 984715 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].I[CH2:17][CH2:18][CH2:19][CH3:20]>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

3

Reactant 2

HCID 10962Butyl iodideHCID 11961473HCID 11961473, compound

Product 1

HCID 22559177HCID 22559177, compound

Procedure

According to the procedure described in the synthesis method of the compound 036 in Example 36 (Preparation Method 5, Step e-1), ethyl 3-(3-bromo-4-hydroxyphenyl)propionate and 1-iodobutane were reacted and treated to obtain ethyl 3-(3-bromo-4-butyloxyphenyl)propionate (400 mg). According to the procedure described in the synthesis method of Compound of Example 001 (Preparation Method 4, Step d-1) with the modifications that the reaction was carried out for 16 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=8:1), the above product was reacted with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (360 mg), 2 M aqueous sodium carbonate (0.9 ml) and (Ph3P)4Pd (110 mg) and treated to obtain the title compound (Intermediate 66, 270 mg).

Workup

  1. customwere reacted
  2. additiontreated

Sources & evidence

ORD record
ord-e7064767dd5f43358df64e3811eae765
Source dataset
uspto-grants-2005_03
Patent number
US06867320B2

Reaction notes

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