Sodium t-butoxide → HCID 67285276, compound

HRID 1618765Notes

Reaction equation

HRID 1618765 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].[CH3:19][C:20]1([CH3:35])[C:24]2=[N:25][CH:26]=[C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[CH:28]=[C:23]2[NH:22][CH2:21]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+]>[CH3:19][C:20]1([CH3:35])[C:24]2=[N:25][CH:26]=[C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[CH:28]=[C:23]2[N:22]([C:2]2[C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:3]=2[CH3:18])[CH2:21]1

Participants

5

Reactant 3

HCID 23676156Sodium t-butoxideHCID 672844994-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)-morpholineHCID 67285251HCID 67285251, compound

Product 1

HCID 67285276HCID 67285276, compound

Reagents, catalysts & solvents 1

HCID 54751079XPhos PalladacycleCatalyst

Procedure

Prepared according to procedure Y using 4-chloro-3-methyl-2-phenyl-1,8-naphthyridine (60 mg, 0.236 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]-pyridin-6-yl)morpholine (55 mg, 0.236 mmol), sodium tert-butoxide (45.3 mg, 0.471 mmol) and XPhos precatalyst (17.4 mg, 0.024 mmol). Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-3-methyl-2-phenyl-1,8-naphthyridine. 1H NMR (400 MHz, chloroform-d) δ ppm 9.10 (1H, dd, J=4.1, 2.0 Hz), 8.16 (1H, dd, J=8.4, 2.0 Hz), 7.67-7.77 (2H, m), 7.62 (1H, d, J=2.3 Hz), 7.40-7.57 (4H, m), 5.80 (1H, d, J=2.3 Hz), 3.79-3.90 (2H, m), 3.70-3.77 (4H, m), 2.88-3.07 (4H, m), 2.36 (3H, s), 1.57 (3H, s), 1.52 (3H, s). Mass Spectrum (ESI) m/e=452.2 (M+1).

Workup

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

Sources & evidence

ORD record
ord-a7c28bc13b344ab195a939af66c2075f
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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