Tetrahydrofuran → HCID 57748783, compound

HRID 1670641Notes

Reaction equation

HRID 1670641 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:12][N:11]([CH3:13])[CH2:10]2)=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1.[F:17][C:18]1[CH:19]=[CH:20][C:21]2=[C:22]([CH:43]=1)[O:23][CH2:24][C:25]1[C:41]([F:42])=[CH:40][CH:39]=[CH:38][C:26]=1/[C:27]/2=[CH:28]\B1OC(C)(C)C(C)(C)O1.O1CCCC1.C[O-].[Na+]>CO.C(OCC)(=O)C.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>[F:17][C:18]1[CH:19]=[CH:20][C:21]2=[C:22]([CH:43]=1)[O:23][CH2:24][C:25]1[C:41]([F:42])=[CH:40][CH:39]=[CH:38][C:26]=1/[C:27]/2=[CH:28]\[C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:12][N:11]([CH3:13])[CH2:10]2)=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 67335783HCID 67335783, compoundHCID 67335785HCID 67335785, compound

Product 1

HCID 57748783HCID 57748783, compoundYield 118.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Purge with nitrogen for five min a mixture of (4-bromo-2-nitro-phenyl)-(1-methyl-azetidin-3-yl)-amine (709 μmol, 203 mg), (E)-3,7-difluoro-11-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-ylmethylene)-6,11-dihydro-dibenzo[b,e]oxepine (723 μmol, 268 mg) in methanol (1.0 mL)/tetrahydrofuran (3.0 mL) (1:3 solvent ratio) in a sealed tube. Add sodium methoxide (1.42 mmol, 77 mg), tetrakis(triphenylphosphine)palladium (35 μmol, 41 mg) and heat at 70° C. overnight. Dilute with ethyl acetate, wash with 10% sodium bicarbonate twice, dry over anhydrous sodium sulfate, filter, and concentrate in vacuo to obtain 377 mg of an orange oil residue. Purify on a 12 g silica gel column eluting with 5% methanol in dichloromethane to obtain the title compound (199 mg, 62%). LC-MS m/z 450.0 [M+H]+.

Workup

  1. customPurge with nitrogen for five min
  2. washwash with 10% sodium bicarbonate twice
  3. dry with materialdry over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-14a819f46b5742628a8ff054ddb6c413
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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