Sodium Carbonate → 5-[4-(4-methoxypyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester

HRID 1892625Notes

Reaction equation

HRID 1892625 reaction equation
O.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1B(O)O.[C:13]([O:17][C:18]([N:20]1[CH2:29][CH2:28][C:27]2[CH:26]=[C:25]3[O:30][CH2:31][O:32][C:24]3=[CH:23][C:22]=2[CH:21]1[CH2:33][C:34]1[CH:39]=[CH:38][C:37](Br)=[CH:36][CH:35]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CC(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:13]([O:17][C:18]([N:20]1[CH2:29][CH2:28][C:27]2[CH:26]=[C:25]3[O:30][CH2:31][O:32][C:24]3=[CH:23][C:22]=2[CH:21]1[CH2:33][C:34]1[CH:35]=[CH:36][C:37]([C:5]2[CH:6]=[N:7][CH:8]=[CH:9][C:4]=2[O:3][CH3:2])=[CH:38][CH:39]=1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 441196714-Methoxypyridine-3-boronic acid monohydrateHCID 597442655-(4-Bromobenzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester

Product 1

HCID 597442885-[4-(4-methoxypyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl esterYield 35%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 4-methoxy pyridine-3-boronic acid hydrate 19 (0.716 g, 4.684 mmol), 5-(4-bromobenzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester 38 (1.043 g, 2.342 mmol), Palladium(II) acetate (0.021 g, 0.094 mmol), triphenylphosphine (0.049 g, 0.187 mmol) and Na2CO3 (0.993 g, 9.368 mmol) in anhydrous 2-propanol (20 mL) was refluxed for 16 h. The reaction mixture was cooled to room temperature, filtered through silica, washed with ethyl acetate. The solvents were concentrated under reduced pressure. The crude residue was purified by flash column chromatography using Acetone-Hexanes (20:80 to 50:60 v/v) to yield 43 (0.389 g, 35%). MS (ES+) m/z 497 (M+Na)+.

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationfiltered through silica
  3. washwashed with ethyl acetate
  4. concentrationThe solvents were concentrated under reduced pressure
  5. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-2175767bd8db47b482bc8eea4a16ad38
Source dataset
uspto-grants-2013_08
Patent number
US08507523B2

Reaction notes

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