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Cesium fluoride → Methyl 2-chloro-4-methyl-6-(3-methyl-1-tosyl-1H-indol-4-yl)nicotinate

HRID 80819
Notes
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Reaction equation

HRID 80819 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[CH:9]=[C:8]([CH3:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2B2OC(C)(C)C(C)(C)O2)[N:17]([S:33]([C:36]2[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH:16]=1.[F-].[Cs+]>CN(C=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>[Cl:1][C:2]1[N:11]=[C:10]([C:22]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:23]=2[C:15]([CH3:14])=[CH:16][N:17]3[S:33]([C:36]2[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH:9]=[C:8]([CH3:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 46911843Methyl 2,6-dichloro-4-methylnicotinateHCID 712404273-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indole

Product 1

HCID 86690266Methyl 2-chloro-4-methyl-6-(3-methyl-1-tosyl-1H-indol-4-yl)nicotinate

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2,6-dichloro-4-methylnicotinate (0.250 g, 1.14 mmol), 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indole (Example 6) (0.514 g, 1.25 mmol), Pd(Ph3P)4 (0.131 g, 0.114 mmol), and CsF (0.345 g, 2.27 mmol), in DMF (5 mL) was heated at 110° C. for 6 h. At that time the vessel was removed from the oil bath and allowed to cool to rt. The mixture was diluted with brine (50 mL) and EtOAc (50 mL). The layers were mixed and then separated. The aqueous layer was further extracted with EtOAc (50 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was then purified via FCC (0-10% EtOAc/heptane) to give the title compound. MS ESI m/z 469.0 & 470.9 (M+H)+.

Workup

  1. customAt that time the vessel was removed from the oil bath
  2. additionThe mixture was diluted with brine (50 mL) and EtOAc (50 mL)
  3. additionThe layers were mixed
  4. customseparated
  5. extractionThe aqueous layer was further extracted with EtOAc (50 mL)
  6. dry with materialthe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was then purified via FCC (0-10% EtOAc/heptane)

Sources & evidence

ORD record
ord-ebf578b16e9146c59bf97ba1928ff07a
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846656B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes