Binap, (A+-)- → HCID 89999965, compound

HRID 333875Notes

Reaction equation

HRID 333875 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:26](Br)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12].C1(P(C2C=CC=CC=2)[C:44]2[CH:53]=[CH:52][C:51]3[C:46](=CC=CC=3)[C:45]=2[C:54]2C3C(=CC=CC=3)C=[CH:56][C:55]=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br-].C1(CCC[Zn+])C=CC=CC=1>O1CCCC1.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].ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:26]([CH2:56][CH2:55][CH2:54][C:45]3[CH:46]=[CH:51][CH:52]=[CH:53][CH:44]=3)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

6

Reactant 3

HCID 634876Binap, (A+-)-HCID 594476151,1-Dimethylethyl 6-(8-((2-benzothiazolylamino)carbonyl)-3,4-dihydro-2(1H)-isoquinolinyl)-3-bromo-2-pyridinecarboxylateHCID 178419781HCID 178419781, compound

Product 1

HCID 89999965HCID 89999965, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of Example 5D (200 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane (28.9 mg) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (22 mg) in tetrahydrofuran (3 mL) was added (3-phenylpropyl)zinc(II) bromide (1.42 mL). The resulting suspension was heated in a Biotage microwave synthesizer at 100° C. for 30 minutes. The reaction mixture was filtered through a sintered glass funnel. The filtrate was concentrated, and the residue was purified by preparative TLC, eluting with 40% acetone in petroleum ether, to provide the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through a sintered glass funnel
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by preparative TLC
  4. washeluting with 40% acetone in petroleum ether

Sources & evidence

ORD record
ord-bc7647311ffc4b4c8853653bb9b3ea2e
Source dataset
uspto-grants-2014_11
Patent number
US08883784B2

Reaction notes

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