Sodium t-butoxide → HCID 67284684, compound

HRID 1618766Notes

Reaction equation

HRID 1618766 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH3:18].[O:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:26]=[C:27]3[NH:33][CH2:32][C:31]4([CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[C:28]3=[N:29][CH:30]=2)[CH2:21][CH2:20]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+]>[CH3:18][C:3]1[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:5][C:6]2[C:11]([C:2]=1[N:33]1[C:27]3[C:28](=[N:29][CH:30]=[C:25]([N:22]4[CH2:23][CH2:24][O:19][CH2:20][CH2:21]4)[CH:26]=3)[C:31]3([CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[CH2:32]1)=[CH:10][CH:9]=[CH:8][N:7]=2

Participants

5

Reactant 3

HCID 23676156Sodium t-butoxideHCID 672847056'-Morpholino-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]HCID 67285251HCID 67285251, compound

Product 1

HCID 67284684HCID 67284684, compound

Reagents, catalysts & solvents 1

HCID 54751079XPhos PalladacycleCatalyst

Procedure

Prepared according to procedure Y using 4-chloro-3-methyl-2-phenyl-1,8-naphthyridine (46.3 mg, 0.182 mmol), 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (50 mg, 0.182 mmol), sodium tert-butoxide (34.9 mg, 0.363 mmol) and XPhos precatalyst (0.0182, 13.5 mg). Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 1′-(3-methyl-2-phenyl-1,8-naphthyridin-4-yl)-6′-(4-morpholinyl)-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine]. 1H NMR (400 MHz, chloroform-d) δ ppm 9.12 (1H, dd, J=4.1, 2.0 Hz), 8.12 (1H, dd, J=8.4, 2.0 Hz), 7.71-7.77 (2H, m), 7.65 (1H, d, J=2.3 Hz), 7.47-7.56 (3H, m), 7.43 (1H, dd, J=8.3, 4.2 Hz), 5.80 (1H, d, J=2.3 Hz), 4.12-4.21 (2H, m), 4.02 (2H, q, J=9.6 Hz), 3.71-3.80 (4H, m), 3.56-3.65 (2H, m, J=11.4, 11.4, 2.5, 2.4 Hz), 2.95-3.05 (4H, m), 2.28-2.41 (5H, m), 1.75-1.90 (2H, m). Mass Spectrum (ESI) m/e=494.2 (M+1).

Workup

  1. customPrepared
  2. customPurification by reverse phase HPLC (10 to 60% acetonitrile in water)

Sources & evidence

ORD record
ord-f1a80d3fc70e44e9b61794560fd79024
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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