Triethylamine → HCID 86761789, compound

HRID 1960142Notes

Reaction equation

HRID 1960142 reaction equation
[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:25]([Cl:26])=[CH:24][C:10]3[NH:11][C:12]([C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19](Br)[CH:18]=4)([F:16])[F:15])=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.C([SiH](CC)CC)C.[CH:47]([O:50][P:51]([O-:56])[O:52][CH:53]([CH3:55])[CH3:54])([CH3:49])[CH3:48]>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].C1(C)C=CC=CC=1>[CH:47]([O:50][P:51]([C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:14]([C:12]2[NH:11][C:10]3[CH:24]=[C:25]([Cl:26])[C:7]([C:4]4[CH:3]=[CH:2][C:1]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[CH:6][CH:5]=4)=[CH:8][C:9]=3[N:13]=2)([F:16])[F:15])[CH:18]=1)(=[O:56])[O:52][CH:53]([CH3:55])[CH3:54])([CH3:49])[CH3:48]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 12052TriethylsilaneHCID 21884976Phosphorous acid, bis(1-methylethyl) esterHCID 67447689HCID 67447689, compound

Product 1

HCID 86761789HCID 86761789, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a microwave reactor vial was added compound 15-1 (60 mg, 0.12 mmol), PdCl2(dppf) (19 mg, 0.024 mmol), triethylamine (50 μL, 0.36 mmol), triethylsilane (8 μL, 0.048 mmol), diisopropylphosphite (24 μL, 0.14 mmol) and 3 mL of toluene. The reaction was run in a microwave reactor for 20 min at 140° C. The reaction mixture was then 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, concentrated in vacuo, and then purified on ISCO (EtOAc/Hexanes=4/1) to yield the title compound 15-2 as a colorless 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. custompurified on ISCO (EtOAc/Hexanes=4/1)

Sources & evidence

ORD record
ord-7f93cef8f0294e999752fe387908c58d
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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