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Methanol → 4-(2-Chloro-5-methylpyridin-4-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

HRID 2374136
Notes
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Reaction equation

HRID 2374136 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[CH3:30])(=[O:21])=[O:20])[CH:7]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:9]=1)=[O:4].Br[C:32]1[C:37]([CH3:38])=[CH:36][N:35]=[C:34]([Cl:39])[CH:33]=1.CO.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC=CC=1.C(OCC)(=O)C.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>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[CH3:30])(=[O:20])=[O:21])[CH:7]=[C:8]([C:32]2[C:37]([CH3:38])=[CH:36][N:35]=[C:34]([Cl:39])[CH:33]=2)[CH:9]=1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 534399184-Bromo-2-chloro-5-methylpyridineHCID 59767810Methyl 1-(mesitylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate

Product 1

HCID 866027194-(2-Chloro-5-methylpyridin-4-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester
Yield 43.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (125 mg, 0.29 mmol, 0.6 equiv.) and 4-bromo-2-chloro-5-methylpyridine (96 mg, 0.47 mmol, 1.0 equiv.) were dissolved in benzene (4 mL). After adding methanol (0.94 mL) and aqueous Na2CO3, Pd(PPh3)4 (108 mg, 0.094 mol, 0.2 equiv.) was then added and the resulting mixture was heated at reflux for 16 hours. The reaction mixture was dissolved in ethyl acetate and washed with water. After drying the organic layer over Na2SO4, the solvent was removed under reduced pressure. The crude material was purified by reversed phase HPLC (acetonitrile/water/TFA), yielding the title compound as a colorless solid (54 mg, 0.125 mmol, HPLC Rt 9.087 min, ES+433.0, ES−431.0).

Workup

  1. additionwas then added
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux for 16 hours
  4. washwashed with water
  5. dry with materialAfter drying the organic layer over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. customThe crude material was purified by reversed phase HPLC (acetonitrile/water/TFA)

Sources & evidence

ORD record
ord-f7afad396acd4b7db3e143fbd08b8443
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07462612B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes