(3-Methoxyphenyl)boronic acid → 5'-(3'-Methoxy-2-methyl-biphenyl-4-ylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid ethyl ester

HRID 2190679Notes

Reaction equation

HRID 2190679 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.[CH2:12]([O:14][C:15]([CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29](=[O:44])[NH:30][C:31]3[CH:36]=[CH:35][C:34](C4C=CC=CC=4)=[C:33]([CH3:43])[CH:32]=3)=[CH:25][N:24]=2)[CH2:19][CH2:18]1)=[O:16])[CH3:13]>>[CH2:12]([O:14][C:15]([CH:17]1[CH2:18][CH2:19][N:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29](=[O:44])[NH:30][C:31]3[CH:36]=[CH:35][C:34]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=4)=[C:33]([CH3:43])[CH:32]=3)=[CH:25][N:24]=2)[CH2:21][CH2:22]1)=[O:16])[CH3:13]

Participants

3

Reactant 2

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 593181715'-(2-methyl-biphenyl-4-ylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-carboxylic acid ethyl ester

Product 1

HCID 593180705'-(3'-Methoxy-2-methyl-biphenyl-4-ylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid ethyl ester

Procedure

5′-(3′-Methoxy-2-methyl-biphenyl-4-ylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester was prepared from F-(4-iodo-3-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4 carboxylic acid ethyl ester and 3-methoxyphenyl boronic acid following a method similar to the one described in the synthesis of 5′-(2-methyl-biphenyl-4-ylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester, above. The product was isolated after silica gel column purification with 20-40% EtOAc in hexanes gradient. HRMS m/z calcd for C28H31N3O4 [M+H]+: 474.2388. Found: 474.2388.

Workup

  1. customThe product was isolated
  2. customafter silica gel column purification with 20-40% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-7bc7d9c34abd40e6b9d7565eb4f13411
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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