Cyclohexanol → HCID 22559286, compound

HRID 984717Notes

Reaction equation

HRID 984717 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].[CH:16]1(O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]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:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 7966CyclohexanolHCID 11961473HCID 11961473, compound

Product 1

HCID 22559286HCID 22559286, compound

Procedure

According to the procedure described in the synthesis method of Intermediate 9 in Reference Example 2 (Step e-2), ethyl 3-(3-bromo-4-hydroxyphenyl)propionate and cyclohexanol were reacted and treated to obtain ethyl 3-(3-bromo-4-cyclohexyloxyphenyl)propionate (355 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 17 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 (330 mg), 2 M aqueous sodium carbonate (0.9 ml) and (Ph3P)4Pd (105 mg) and treated to obtain the title compound (Intermediate 68, 260 mg).

Workup

  1. customwere reacted
  2. additiontreated

Sources & evidence

ORD record
ord-025f3de444c048b6856cfa82e4add8b9
Source dataset
uspto-grants-2005_03
Patent number
US06867320B2

Reaction notes

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