Sodium Carbonate → HCID 86762017, compound

HRID 1400102Notes

Reaction equation

HRID 1400102 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH:14]=2)O1.Br[C:24]1[CH:36]=[CH:35][C:27]2[S:28][C:29]([C:31]([O:33][CH3:34])=[O:32])=[CH:30][C:26]=2[CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>COCCOC.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>[CH3:34][O:33][C:31]([C:29]1[S:28][C:27]2[CH:35]=[CH:36][C:24]([C:9]3[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH:14]=3)=[CH:25][C:26]=2[CH:30]=1)=[O:32]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2824065methyl 5-bromo-1-benzothiophene-2-carboxylateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 86762017HCID 86762017, compoundYield 165.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1.1 g of tert-butyl 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (purity 70%), 0.7 g of methyl 5-bromobenzo[b]thiophene-2-carboxylate, 0.15 g of PalladiumTetrakis (PdP(Ph3)4), 5.5 ml of 2M sodium carbonate solution and 0.42 g of lithium chloride are placed in 30 ml of DME in a round-bottomed flask under a stream of nitrogen. The mixture is heated at the reflux temperature for 3 hours. The solvent is evaporated off and the residue is dissolved in 35 ml of ethyl acetate. This solution is washed with 2M sodium carbonate solution. The organic phase is dried over Na2SO4, filtered and evaporated under vacuum. 1.6 g of an oily material are isolated, and this material is purified by flash chromatography on a Biotage® column, using 98/2 cyclohexane/ethyl acetate as eluent. 0.45 g of a yellowish solid is isolated.

Workup

  1. temperatureThe mixture is heated at the reflux temperature for 3 hours
  2. customThe solvent is evaporated off
  3. dissolutionthe residue is dissolved in 35 ml of ethyl acetate
  4. washThis solution is washed with 2M sodium carbonate solution
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-eb387a4764f64040817497d4f6eac024
Source dataset
uspto-grants-2014_12
Patent number
US08906924B2

Reaction notes

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