Dimethylformamide → HCID 70855547, compound

HRID 591040Notes

Reaction equation

HRID 591040 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[O:21][CH2:20][CH2:19][CH2:18]3)O1.Br[C:27]1[C:28]2[C:45]([CH3:46])=[CH:44][CH:43]=[CH:42][C:29]=2[S:30][C:31]=1[CH:32]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[C:33]([O:35][CH3:36])=[O:34].CN(C)C=O>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:38]([O:37][CH:32]([C:31]1[S:30][C:29]2[CH:42]=[CH:43][CH:44]=[C:45]([CH3:46])[C:28]=2[C:27]=1[C:15]1[CH:24]=[CH:23][C:22]2[O:21][CH2:20][CH2:19][CH2:18][C:17]=2[CH:16]=1)[C:33]([O:35][CH3:36])=[O:34])([CH3:41])([CH3:40])[CH3:39]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 438110342-(3,4-dihydro-2H-1-benzopyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 70855555HCID 70855555, compound

Product 1

HCID 70855547HCID 70855547, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Under a nitrogen atmosphere, sodium carbonate (33 mg, 0.3 mmol), palladium tetrakis(triphenylphosphine) (35 mg, 0.03 mmol) and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (78 mg, 0.3 mmol) were added to a solution of methyl (3-bromo-4-methyl-benzo[b]thiophen-2-yl)-tert-butoxy-acetate (23i) (100 mg, 0.28 mmol) in a mixture of water (1 mL) and N,N(-dimethylformamide (3 mL). The mixture was heated at 100° C. for 1 hour. The mixture was then cooled at room temperature, concentrated in vacuo and water (30 mL) was added. The aqueous layer was extracted with ethyl acetate (2×30 mL). The organic layer was washed with brine (30 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired product (23j) as a white solid (65 mg, 0.15 mmol, 57%).

Workup

  1. temperatureThe mixture was then cooled at room temperature
  2. concentrationconcentrated in vacuo and water (30 mL)
  3. additionwas added
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×30 mL)
  5. washThe organic layer was washed with brine (30 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

Sources & evidence

ORD record
ord-847e484d225c42a7a6c6fb629afb3e55
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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