Ethyl 2-(5-bromopyridin-3-yl)acetate → (5-{2-[(N-Acetyl-N-benzyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid

HRID 554634Notes

Reaction equation

HRID 554634 reaction equation
[CH2:1]([N:8]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1B1OC(C)(C)C(C)(C)O1)[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:34][C:35](=[O:44])[CH2:36][C:37]1[CH:38]=[N:39][CH:40]=[C:41](Br)[CH:42]=1)C>>[C:9]([N:8]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:41]1[CH:42]=[C:37]([CH2:36][C:35]([OH:44])=[O:34])[CH:38]=[N:39][CH:40]=1)[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:11])[CH3:10]

Participants

3

Reactant 2

HCID 54116619Ethyl 2-(5-bromopyridin-3-yl)acetateHCID 67212483N-Benzyl-N-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-acetamide

Product 1

HCID 45138774(5-{2-[(N-Acetyl-N-benzyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid

Procedure

N-Benzyl-N-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-acetamide and (5-bromo-pyridin-3-yl)-acetic acid ethyl ester were reacted as described in Example 17, Step 4 and the product was hydrolyzed to the acid as described in Example 17, Step 5.

Sources & evidence

ORD record
ord-630f4825c7544008800fa85c4cee58a9
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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