Sodium t-butoxide → HCID 67284808, compound

HRID 1618723Notes

Reaction equation

HRID 1618723 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][C:16]([CH3:21])([CH3:20])[CH2:15]2)[C:3]=1[CH3:22].[CH3:23][C:24]1([CH3:39])[C:28]2=[N:29][CH:30]=[C:31]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[CH:32]=[C:27]2[NH:26][CH2:25]1.CC(C)([O-])C.[Na+]>CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=C(C(C)C)C=1)C.C1C=[C-]C(CCN)=CC=1.Cl[Pd+].C1(C)C=CC=CC=1>[CH3:20][C:16]1([CH3:21])[O:17][CH2:18][CH2:19][N:14]([C:4]2[C:3]([CH3:22])=[C:2]([N:26]3[C:27]4[C:28](=[N:29][CH:30]=[C:31]([N:33]5[CH2:34][CH2:35][O:36][CH2:37][CH2:38]5)[CH:32]=4)[C:24]([CH3:39])([CH3:23])[CH2:25]3)[C:11]3[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=3[F:12])[N:5]=2)[CH2:15]1

Participants

6

Reactant 3

HCID 23676156Sodium t-butoxideHCID 672844994-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)-morpholineHCID 67284943HCID 67284943, compound

Product 1

HCID 67284808HCID 67284808, compound

Reagents, catalysts & solvents 2

HCID 54751079XPhos PalladacycleCatalystHCID 1140TolueneSolvent

Procedure

Preparing according to procedure Y by using 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)-2,2-dimethylmorpholine (70.0 mg, 0.21 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine (50 mg, 0.21 mmol), sodium tert-butoxide (20.60 mg, 0.21 mmol) and XPhos precatalyst (16 mg, 0.02 mmol) in toluene (4 mL) at reflux for 2 h. Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 2-(2,2-dimethyl-4-morpholinyl)-4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-3-methylquinoline. 1H NMR (400 MHz, chloroform-d) δ ppm 7.56 (1H, d, J=2.3 Hz), 7.34-7.40 (1H, m), 6.69-6.82 (1H, m), 5.67 (1H, d, J=2.3 Hz), 3.90-4.02 (2H, m), 3.77-3.81 (1H, m), 3.71-3.76 (4H, m), 3.66 (1H, d, J=9.0 Hz), 3.27-3.37 (2H, m), 3.10-3.23 (2H, m), 2.92-3.01 (4H, m), 2.28 (3H, s), 1.53 (3H, d, J=0.8 Hz), 1.49 (3H, s), 1.40 (3H, s), 1.35 (3H, s). Mass Spectrum (ESI) m/e=524.2 (M+1).

Workup

  1. customPreparing
  2. temperatureat reflux for 2 h
  3. customPurification by reverse phase HPLC (10 to 60% acetonitrile in water)

Sources & evidence

ORD record
ord-db7edb5a52054f5cb2e30e27f59a238a
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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