Sodium Carbonate → HCID 59526292, compound

HRID 385720Notes

Reaction equation

HRID 385720 reaction equation
Br[C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([C:10]([NH2:12])=[O:11])[CH:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][C:24]([C:27]3([OH:31])[CH2:30][O:29][CH2:28]3)=[CH:23][CH:22]=2)O1.C([O-])([O-])=O.[Na+].[Na+].[NH4+].[Cl-]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[OH:31][C:27]1([C:24]2[CH:25]=[CH:26][C:21]([C:2]3[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([C:10]([NH2:12])=[O:11])[CH:3]=3)=[CH:22][CH:23]=2)[CH2:30][O:29][CH2:28]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 534029485-Bromo-2-nitrothiophene-3-carboxamide2×HCID 583822471093878-29-5

Product 1

HCID 59526292HCID 59526292, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-2-nitrothiophene-3-carboxamide (Intermediate 10, Step 4) (1.44 g, 5.74 mmol), 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxetan-3-ol (1.821 g, 6.60 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.331 g, 0.287 mmol) were taken up in THF (25 mL)/2 N Na2CO3 (10 mL) and the reaction mixture was stirred at 80° C. overnight. After cooling to room temperature, saturated NH4Cl and EtOAc were added. The resulting precipitate was collected by filtration, washed with water and dried to give 5-[4-(3-hydroxyoxetan-3-yl)phenyl]-2-nitrothiophene-3-carboxamide as a brown solid (batch 1). The organic phase from the filtrate was separated, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo while loading onto silica. Purification of the residue by flash silica gel column chromatography (12-100% EtOAc-hexanes followed by 0-10% MeOH-EtOAc) gave the title compound as an orange solid after recrystallising from EtOH (batch 2).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-1f209864d480483092592b5c90e3264b
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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