HCID 11961473, compound → HCID 22559071, compound

HRID 984716Notes

Reaction equation

HRID 984716 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].[Br-].[CH2:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>>[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][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 11961473HCID 11961473, compoundHCID 22031976HCID 22031976, compound

Product 1

HCID 22559071HCID 22559071, compound

Procedure

According to the procedure described in the synthesis method of Intermediate 8 in Reference Example 2 (Step e-1), ethyl 3-(3-bromo-4-hydroxyphenyl)propionate and cyclopentane bromide were reacted and treated to obtain ethyl 3-(3-bromo-4-cyclopentyloxyphenyl)propionate (410 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 18 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 (396 mg), 2 M aqueous sodium carbonate (1.0 ml) and (Ph3P)4Pd (110 mg) and treated to obtain the title compound (Intermediate 67, 313 mg).

Workup

  1. customwere reacted
  2. additiontreated

Sources & evidence

ORD record
ord-009ea99fa28c4784be2e05c80d990447
Source dataset
uspto-grants-2005_03
Patent number
US06867320B2

Reaction notes

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