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Sodium Carbonate → (1S,2R)-3-Fluoro-4'-(2-hydroxy-1-methyl-4-pyridin-3-yl-butoxy)biphenyl-4-sulfonic acid amide

HRID 380045
Notes
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Reaction equation

HRID 380045 reaction equation
[OH:1][C@H:2]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C@H:3]([CH3:14])[O:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1.Br[C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[C:26]([F:34])[CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[F:34][C:26]1[CH:25]=[C:24]([C:8]2[CH:9]=[CH:10][C:5]([O:4][C@@H:3]([CH3:14])[C@H:2]([OH:1])[CH2:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:6][CH:7]=2)[CH:29]=[CH:28][C:27]=1[S:30]([NH2:33])(=[O:31])=[O:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27789034-Bromo-2-fluorobenzenesulphonamideHCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

Product 1

HCID 57126424(1S,2R)-3-Fluoro-4'-(2-hydroxy-1-methyl-4-pyridin-3-yl-butoxy)biphenyl-4-sulfonic acid amideYield 38.5%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Prepared according to the method described in Example 12b) from 4-[(2S,3R)-5-(pyridin-3-yl)-3-hydroxypent-2-yloxy]benzeneboronic acid (0.20 g, Example 33), 4-bromo-2-fluorophenylsulfonic acid amide (0.20 g), ethanol (3 ml), 2M aqueous sodium carbonate (1.0 ml) and tetrakis(triphenylphosphine)palladium (0) (0.03 g) with heating at 90° C. for 3 hours. After work-up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane, followed by recrystalisation from aqueous ethanol, to give the title compound as a solid (0.11 g).

Workup

  1. customPrepared
  2. customAfter work-up, the residue was purified by normal-phase HPLC
  3. washeluting with a gradient of 0-25% ethanol in dichloromethane
  4. customfollowed by recrystalisation from aqueous ethanol

Sources & evidence

ORD record
ord-315973d6cec8488f83781a6ff85a4cfa
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06300352B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes