Sodium Carbonate → HCID 70819378, compound

HRID 591029Notes

Reaction equation

HRID 591029 reaction equation
Br[C:2]1[O:3][C:4]2[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=2[C:6]=1[CH:7]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:36]2[CH:37]=[C:38]3[C:43](=[CH:44][CH:45]=2)[O:42][CH2:41][CH2:40][CH2:39]3)O1>C1(C)C=CC=CC=1.O.C(O)C.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:14]([O:13][CH:7]([C:6]1[C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]=2[O:3][C:2]=1[C:36]1[CH:45]=[CH:44][C:43]2[O:42][CH2:41][CH2:40][CH2:39][C:38]=2[CH:37]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])([CH3:17])([CH3:16])[CH3:15]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 438110342-(3,4-dihydro-2H-1-benzopyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 70819417HCID 70819417, compound

Product 1

HCID 70819378HCID 70819378, compoundYield 53.6%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of ethyl 2-(2-bromo-1-benzofuran-3-yl)-2-(tert-butoxy)acetate (20c) (100 mg, 0.28 mmol), sodium carbonate (120 mg, 1.13 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (132 mg, 0.51 mmol) and palladium tetrakis(triphenylphosphine) (16 mg, 0.01 mmol) in toluene (1.26 mL), water (0.50 mL) and ethanol (0.60 mL) was heated at 95° C. for 24 hours. After cooling to room temperature, the mixture was poured into water (2 mL). The aqueous layer was extracted with toluene (2×5 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (cyclohexane/ethyl acetate 80/20) to provide the desired product (20d) (61 mg, 0.15 mmol, 53%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous layer was extracted with toluene (2×5 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC (cyclohexane/ethyl acetate 80/20)

Sources & evidence

ORD record
ord-3763de1ab35745799ff455d7f1a8fd42
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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