Benzylamine → HCID 44180513, compound

HRID 1042030Notes

Reaction equation

HRID 1042030 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[O:13][C:14]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:15][C:16](=[O:17])[C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[CH2:42]([NH2:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.N12CCCN=C1CCCCC2.[O:61]1CCC[CH2:62]1>CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[CH2:42]([NH:49][C:62](=[O:61])[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[O:13][C:14]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:15][C:16](=[O:17])[C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 44181722HCID 44181722, compound

Product 1

HCID 44180513HCID 44180513, compound

Reagents, catalysts & solvents 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)Catalyst

Conditions

Temperature
170 °C

Procedure

A 2 mL conical microwave vial was charged with a magnetic stirring bar, 3-(4-chlorophenyl)-5-morpholino-7H-thieno[3,2-b]pyran-7-one (17) (80 mg, 230 μmol), trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium (II) (6 mg, 7 μmol), tri-tert-butylphosphonium tetrafluoroborate (4 mg, 14 μmol), molybdenumhexacarbonyl (61 mg, 230 μmol), tetrahydrofuran (500 μL), benzyl amine (75 μL, 690 μmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (103 μL, 690 μmol). The reaction mixture was magnetically stirred and heated via microwave irradiation for 15 minutes at 170° C. Upon cooling to room temperature, the reaction was concentrated in vacuo and purified using high-pressure liquid chromatography to give N-benzyl-4-(5-morpholino-7-oxo-7H-thieno[3,2-b]pyran-3-yl)benzamide (50).

Workup

  1. additionA 2 mL conical microwave vial was charged with a magnetic stirring bar
  2. temperatureUpon cooling to room temperature
  3. concentrationthe reaction was concentrated in vacuo
  4. custompurified

Sources & evidence

ORD record
ord-cd0573da792b44c68d2c408008060736
Source dataset
uspto-grants-2013_10
Patent number
US08557807B2

Reaction notes

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