Ethyl 4-(bromomethyl)benzoate → HCID 67606146, compound

HRID 1024740Notes

Reaction equation

HRID 1024740 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:34]([O:36][C:37](=[O:46])[C:38]1[CH:43]=[CH:42][C:41]([CH2:44]Br)=[CH:40][CH:39]=1)[CH3:35]>>[CH2:34]([O:36][C:37](=[O:46])[C:38]1[CH:43]=[CH:42][C:41]([CH2:44][O:22][C:20]2[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:17]=[C:16]([C:15](=[O:32])[NH:14][CH:11]3[CH2:12][CH2:13][CH:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:33])[CH2:9][CH2:10]3)[CH:21]=2)=[CH:40][CH:39]=1)[CH3:35]

Participants

3

Reactant 2

HCID 954261Ethyl 4-(bromomethyl)benzoateHCID 66818660HCID 66818660, compound

Product 1

HCID 67606146HCID 67606146, compoundYield 81.2%

Procedure

Using 1.2 g (2.65 mmol) of {4-[3-(4-cyano-phenoxy)-5-hydroxy-benzoylamino]-cyclohexyl}-carbamic acid tert-butyl ester and 4-bromomethyl-benzoic acid ethyl ester (0.644 g, 2.65 mmol) and following the procedure of Example 42(b) afforded 1.32 g of the required product. Percentage purity (LCMS): 84.4%, (M+1)=613.2+1.

Sources & evidence

ORD record
ord-d73e8d121e664dd6b008ee6a30a14399
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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