Water → methyl 2-(tert-butoxy)-2-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)thieno[3,2-f]quinolin-2-yl]acetate

HRID 591019Notes

Reaction equation

HRID 591019 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].O.Br[C:9]1[C:13]2=[C:14]3[C:19](=[CH:20][CH:21]=[C:12]2[S:11][C:10]=1[CH:22]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:23]([O:25][CH3:26])=[O:24])[N:18]=[CH:17][CH:16]=[CH:15]3.CC1(C)C(C)(C)OB([C:40]2[CH:41]=[C:42]3[C:47](=[CH:48][CH:49]=2)[O:46][CH2:45][CH2:44][CH2:43]3)O1>CN(C)C=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:28]([O:27][CH:22]([C:10]1[S:11][C:12]2[C:13](=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)[C:9]=1[C:40]1[CH:49]=[CH:48][C:47]2[O:46][CH2:45][CH2:44][CH2:43][C:42]=2[CH:41]=1)[C:23]([O:25][CH3:26])=[O:24])([CH3:31])([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 438110342-(3,4-dihydro-2H-1-benzopyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86717834Methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-(tert-butoxy)acetate

Product 1

HCID 70818457methyl 2-(tert-butoxy)-2-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)thieno[3,2-f]quinolin-2-yl]acetateYield 31%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Under argon atmosphere, sodium carbonate (15.7 mg, 0.15 mmol), water (0.8 mL), and methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-(tert-butoxy)acetate (16i) (55 mg, 0.14 mmol) were added to a solution of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (38.5 mg, 0.15 mmol) in N,N-dimethylformamide (3 mL). The solution was degassed under argon and palladium tetrakis(triphenylphosphine) (47 mg, 0.04 mmol) was added. The mixture was heated at 100° C. for 4 hours. The mixture was then cooled at room temperature, water was added and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by preparative TLC (cyclohexane/ethyl acetate 70/30) to afford the desired product (16j) (19 mg, 0.04 mmol, 31%).

Workup

  1. customThe solution was degassed under argon
  2. temperatureThe mixture was then cooled at room temperature
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by preparative TLC (cyclohexane/ethyl acetate 70/30)

Sources & evidence

ORD record
ord-44ec1765b5af4e0da350e6daa6753e03
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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