Ethyl 2-(5-bromopyridin-3-yl)acetate → (5-{2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-tert-butylcarbamoyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

HRID 554604Notes

Reaction equation

HRID 554604 reaction equation
[CH2:1]([N:8]([CH2:14][C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][C:27]=1B1OC(C)(C)C(C)(C)O1)[C:18]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:9]([CH:11]1[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:37]([O:39][C:40](=[O:49])[CH2:41][C:42]1[CH:43]=[N:44][CH:45]=[C:46](Br)[CH:47]=1)[CH3:38]>>[CH2:37]([O:39][C:40](=[O:49])[CH2:41][C:42]1[CH:43]=[N:44][CH:45]=[C:46]([C:27]2[CH:26]=[CH:25][C:17]([C:18](=[O:19])[NH:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[CH:16][C:15]=2[CH2:14][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]([CH:11]2[CH2:12][CH2:13]2)=[O:10])[CH:47]=1)[CH3:38]

Participants

3

Reactant 2

HCID 54116619Ethyl 2-(5-bromopyridin-3-yl)acetateHCID 672126853-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-N-tert-butyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide

Product 1

HCID 67212635(5-{2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-tert-butylcarbamoyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

Procedure

3-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-N-tert-butyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide and (5-bromo-pyridin-3-yl)-acetic acid ethyl ester were reacted as described in Example 3, Step 6 to provide (5-{2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-tert-butylcarbamoyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester.

Sources & evidence

ORD record
ord-d1ade0c250a24544ae347a1cd8809dd1
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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