1,2-Dimethoxyethane → 2'-Methoxy-5'-(2-methyl-4-morpholin-4-yl-phenylcarbamoyl)-biphenyl-4-carboxylic acid

HRID 1678529Notes

Reaction equation

HRID 1678529 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][C:9]=1[CH3:20])=[O:6].C([O:28][C:29]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)=[O:30])C.COCCOC.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH3:25][O:24][C:23]1[CH:22]=[CH:21][C:4]([C:5](=[O:6])[NH:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:10][C:9]=2[CH3:20])=[CH:3][C:2]=1[C:34]1[CH:35]=[CH:36][C:31]([C:29]([OH:30])=[O:28])=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 27343504-Ethoxycarbonylphenylboronic acidHCID 673739843-Bromo-4-methoxy-N-(2-methyl-4-morpholin-4-yl-phenyl)-benzamide

Product 1

HCID 673743492'-Methoxy-5'-(2-methyl-4-morpholin-4-yl-phenylcarbamoyl)-biphenyl-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-Bromo-4-methoxy-N-(2-methyl-4-morpholin-4-yl-phenyl)-benzamide (432 mg) and 4-(ethoxycarbonyl)-phenyl boronic acid (311 mg) in 2:1 DME:water (15 ml) containing cesium carbonate (697 mg) and tetrakis(triphenylphosphine)palladium0 (127 mg) was heated to reflux for 18 h.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h.

Sources & evidence

ORD record
ord-96690057a1ce48d18410318896f3af9d
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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