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Triethylamine → [3-(5-biphenyl-4-yl-6-fluoro-1H-benzoimidazol-2-yloxy)-phenyl]-phosphonic acid diisopropyl ester

HRID 1960136
Notes
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Reaction equation

HRID 1960136 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:23]([F:24])=[CH:22][C:10]3[NH:11][C:12]([O:14][C:15]4[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=4)=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.C([SiH](CC)CC)C.[CH:45]([O:48][P:49]([O-:54])[O:50][CH:51]([CH3:53])[CH3:52])([CH3:47])[CH3:46]>C1(C)C=CC=CC=1.CN(C=O)C.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:45]([O:48][P:49]([C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][C:12]2[NH:11][C:10]3[CH:22]=[C:23]([F:24])[C:7]([C:4]4[CH:5]=[CH:6][C:1]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)=[CH:2][CH:3]=4)=[CH:8][C:9]=3[N:13]=2)[CH:16]=1)(=[O:54])[O:50][CH:51]([CH3:53])[CH3:52])([CH3:47])[CH3:46]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 12052TriethylsilaneHCID 21884976Phosphorous acid, bis(1-methylethyl) esterHCID 674463835-Biphenyl-4-yl-2-(3-bromo-phenoxy)-6-fluoro-1H-benzoimidazole

Product 1

HCID 86658719[3-(5-biphenyl-4-yl-6-fluoro-1H-benzoimidazol-2-yloxy)-phenyl]-phosphonic acid diisopropyl ester

Reagents, catalysts & solvents

4
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a microwave reactor vial was added compound 13-7 (107 mg, 0.23 mmol), PdCl2(dppf) (34 mg, 0.047 mmol), triethylamine (0.1 mL, 0.69 mmol), triethylsilane (15 μL, 0.092 mmol), diisopropylphosphite (46 μL, 0.28 mmol) in 3 mL of toluene and 0.5 mL of DMF. The reaction was run in a microwave reactor for 7 min at 140° C. The reaction mixture was diluted with EtOAc (50 mL) and washed three times with 50 mL portions of saturated aqueous ammonium chloride. The combined organic layers were dried over MgSO4 filtered and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (eluting with EtOAc/Hexanes=4/1) to yield title compound 13-8 as a brown oil.

Workup

  1. washwashed three times with 50 mL portions of saturated aqueous ammonium chloride
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by silica gel column chromatography (eluting with EtOAc/Hexanes=4/1)

Sources & evidence

ORD record
ord-4115b0955075453c8e912a2df20138a1
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08410284B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes