2-(Di-tert-butylphosphino)biphenyl → HCID 86721469, compound

HRID 869610Notes

Reaction equation

HRID 869610 reaction equation
Br[C:2]1[C:3]2[N:4]([C:8]([CH2:14][C:15]3[CH:34]=[CH:33][C:18]4/[C:19](=[C:29](/[CH3:32])\[C:30]#[N:31])/[C:20]5[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=5[O:22][CH2:23][C:17]=4[CH:16]=3)=[C:9]([CH:11]3[CH2:13][CH2:12]3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].[CH3:62][NH:63][CH3:64].C1COCC1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:11]1([C:9]2[N:10]=[C:3]3[C:2]([N:63]([CH3:64])[CH3:62])=[CH:7][CH:6]=[CH:5][N:4]3[C:8]=2[CH2:14][C:15]2[CH:34]=[CH:33][C:18]3/[C:19](=[C:29](/[CH3:32])\[C:30]#[N:31])/[C:20]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=4[O:22][CH2:23][C:17]=3[CH:16]=2)[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 22320367Dimethylamine tetrahydrofuranHCID 23676156Sodium t-butoxideHCID 86721470HCID 86721470, compound

Product 1

HCID 86721469HCID 86721469, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

(E)-2-{8-[(8-bromo-2-cyclopropylimidazo[1,2-a]pyridin-3-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (0.36 g, 0.69 mmol) obtained in Reference Example 14C, step 4 was dissolved in toluene (14 mL), Pd2(dba)3 (0.13 g, 0.14 mmol), 2-(di-tert-butylphosphino)biphenyl (0.04 g, 0.14 mmol), sodium tert-butoxide (0.13 g, 1.4 mmol) and 2 mol/L dimethylamine THF solution (4.5 mL, 9.0 mmol) were added, and the mixture was stirred with heating at 120° C. for 2.5 hr in an Emrys Optimizer microwave synthesizer. The mixture was filtered through celite, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (heptane/ethyl acetate=100/0 v/v-70/30 v/v) to give the title compound (0.10 g, 29%).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (heptane/ethyl acetate=100/0 v/v-70/30 v/v)

Sources & evidence

ORD record
ord-a230b391a6f644a2815bba7ef8ecf6d2
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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