Cesium fluoride → Methyl 3-formyl-1-(3-(naphthalen-1-yloxy)propyl)-4-o-tolyl-1h-indole-2-carboxylate

HRID 533261Notes

Reaction equation

HRID 533261 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:29]=[O:30])=[C:5]([C:25]([O:27][CH3:28])=[O:26])[N:6]2[CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.[C:31]1([CH3:40])[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1B(O)O.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[Cs+]>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:29]([C:4]1[C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[CH3:40])[N:6]([CH2:11][CH2:12][CH2:13][O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:5]=1[C:25]([O:27][CH3:28])=[O:26])=[O:30]

Participants

7

Reactant 4

HCID 25953Cesium fluorideHCID 27332672-Methylphenyl boronic acidHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 87353272Methyl 4-bromo-3-formyl-1-[3-(1-naphthalenyloxy)propyl]-1H-indole-2-carboxylate

Product 1

HCID 87353147Methyl 3-formyl-1-(3-(naphthalen-1-yloxy)propyl)-4-o-tolyl-1h-indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of EXAMPLE 107B (0.5 g) and o-tolylboronic acid (175 mg) in tetrahydrofuran (5 ml) was added tris(dibenzylideneacetone)dipalladium(0) (25 mg), tri-t-butyl-phosphonium tetrafluoroborate (16 mg) and CsF (489 mg). The mixture was purged with Argon and stirred at room temperature for 24 hours. The mixture was diluted with ethyl acetate (200 mL) and washed with water and brine and dried over Na2SO4. After filtration, concentration of the solvent and column purification (5% ethyl acetate in hexane) provided EXAMPLE 107C.

Workup

  1. customThe mixture was purged with Argon
  2. additionThe mixture was diluted with ethyl acetate (200 mL)
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration, concentration of the solvent and column purification (5% ethyl acetate in hexane)
  6. customprovided EXAMPLE 107C

Sources & evidence

ORD record
ord-8096cc126e8b4097a8fda770ff4a741a
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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