Triethylamine → HCID 86761788, compound

HRID 1960140Notes

Reaction equation

HRID 1960140 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:24]([Cl:25])=[CH:23][C:10]3[NH:11][C:12]([C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18](Br)[CH:17]=4)=[O: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:46]([O:49][P:50]([O-:55])[O:51][CH:52]([CH3:54])[CH3:53])([CH3:48])[CH3:47]>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:46]([O:49][P:50]([C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([C:14]([C:12]2[NH:11][C:10]3[CH:23]=[C:24]([Cl:25])[C:7]([C:4]4[CH:5]=[CH:6][C:1]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)=[CH:2][CH:3]=4)=[CH:8][C:9]=3[N:13]=2)=[O:15])[CH:21]=1)(=[O:55])[O:51][CH:52]([CH3:54])[CH3:53])([CH3:48])[CH3:47]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 12052TriethylsilaneHCID 21884976Phosphorous acid, bis(1-methylethyl) esterHCID 67445972HCID 67445972, compound

Product 1

HCID 86761788HCID 86761788, 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 14-2 (150 mg, 0.31 mmol), PdCl2(dppf) (50 mg, 0.061 mmol), triethylamine (0.13 mL, 0.93 mmol), triethylsilane (19 μL, 0.12 mmol), diisopropylphosphite (62 μL, 0.37 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=1/1) to yield title compound 14-3 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. custompurified on ISCO (EtOAc/Hexanes=1/1)

Sources & evidence

ORD record
ord-908e575fd2fb40cf9f1f78cabe775a0e
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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