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Water → HCID 70818582, compound

HRID 591062
Notes
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Reaction equation

HRID 591062 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].O.Br[C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1.[C:20]([O:24][CH:25]([C:31]1[C:35](B2OC(C)(C)C(C)(C)O2)=[C:34]([CH3:45])[S:33][C:32]=1[CH3:46])[C:26]([O:28][CH2:29][CH3:30])=[O:27])([CH3:23])([CH3:22])[CH3:21]>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:20]([O:24][CH:25]([C:31]1[C:35]([C:9]2[CH:10]=[CH:11][C:12]3[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=3[CH:19]=2)=[C:34]([CH3:45])[S:33][C:32]=1[CH3:46])[C:26]([O:28][CH2:29][CH3:30])=[O:27])([CH3:23])([CH3:22])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 162181426-Bromo-2H-1,4-benzoxazin-3(4H)-oneHCID 70818507HCID 70818507, compound

Product 1

HCID 70818582HCID 70818582, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Under argon atmosphere, sodium carbonate (11.2 mg, 0.11 mmol), water (0.7 mL), and 6-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one (24.2 mg, 0.11 mmol) were added to a solution of ethyl 2-(tert-butoxy)-2-[2,5-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl]acetate (28f) (48 mg, 0.10 mmol) in N,N-dimethylformamide (2.1 mL). The solution was degassed under argon and palladium tetrakis(triphenylphosphine) (23.4 mg, 0.02 mmol) was added. The mixture was heated at 100° C. for 15 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 (35a) (14 mg, 0.03 mmol, 33%).

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-45fe52d8a88a4d7f82422429df92820b
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238026B2

Reaction notes

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