Morpholine → HCID 50938606, compound

HRID 1618567Notes

Reaction equation

HRID 1618567 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([N:20]1[C:28]3[C:23](=[CH:24][CH:25]=[C:26](I)[CH:27]=3)[C:22]([CH3:31])([CH3:30])[CH2:21]1)=[C:5]([CH3:19])[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])=[N:7]2.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC(C)([O-])C.[Na+]>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]>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([N:20]1[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[CH:27]=3)[C:22]([CH3:31])([CH3:30])[CH2:21]1)=[C:5]([CH3:19])[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])=[N:7]2

Participants

7

Reactant 4

HCID 8083MorpholineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 67284548HCID 67284548, compound

Product 1

HCID 50938606HCID 50938606, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Prepared according to procedure N using 5-chloro-2-(2-fluorophenyl)-4-(6-iodo-3,3-dimethylindolin-1-yl)-3-methylquinoline (14.4 mg, 0.027 mmol) (described herein), morpholine (5 μL, 0.05 mmol), Pd2dba3 (3.64 mg, 4.0 μmol), 2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl (3.79 mg, 8.0 μmol), and sodium tert-butoxide (7.65 mg, 0.080 mmol) in toluene (1.0 mL). The reaction mixture was stirred at 100° C. for 1 h. Purification afforded 5-chloro-4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2-(2-fluorophenyl)-3-methylquinoline as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.12 (1H, dd, J=6.5, 3.1 Hz), 7.55-7.69 (3H, m), 7.41-7.52 (1H, m), 7.30-7.38 (1H, m), 7.14-7.23 (1H, m), 7.04 (1H, d, J=8.0 Hz), 6.25 (1H, d), 5.59 (1H, d), 3.98-4.08 (1H, m), 3.76 (4H, br. s.), 3.54 (1H, d, J=1.8 Hz), 3.01 (4H, br. s.), 2.12-2.25 (3H, m), 1.47-1.55 (3H, m), 1.42 (3H, s). Mass Spectrum (ESI) m/e=502 (M+1).

Workup

  1. customPrepared
  2. customPurification

Sources & evidence

ORD record
ord-b66de645a4934bf5bb0bac6508849871
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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