Sodium t-butoxide → HCID 50939210, compound

HRID 1618796Notes

Reaction equation

HRID 1618796 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH:12]2[CH2:14][CH2:13]2)[C:3]=1[CH3:15].[CH3:16][C:17]1([CH3:32])[C:21]2=[N:22][CH:23]=[C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:25]=[C:20]2[NH:19][CH2:18]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>[CH:12]1([C:4]2[C:3]([CH3:15])=[C:2]([N:19]3[C:20]4[C:21](=[N:22][CH:23]=[C:24]([N:26]5[CH2:27][CH2:28][O:29][CH2:30][CH2:31]5)[CH:25]=4)[C:17]([CH3:32])([CH3:16])[CH2:18]3)[C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 23676156Sodium t-butoxideHCID 66631833HCID 66631833, compoundHCID 672844994-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)-morpholine

Product 1

HCID 50939210HCID 50939210, compound

Reagents, catalysts & solvents 2

HCID 54751079XPhos PalladacycleCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to procedure Y using 4-chloro-2-cyclopropyl-3-methyl-1,8-naphthyridine (40 mg, 0.183 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine (42.7 mg, 0.183 mmol), XPhos precatalyst (13.52 mg, 0.018 mmol) and sodium tert-butoxide (35.2 mg, 0.366 mmol) by heating in toluene (4 mL) for 2 hours at 110° C. Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 2-cyclopropyl-4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-3-methyl-1,8-naphthyridine. 1H NMR (400 MHz, chloroform-d) δ ppm 8.98 (1H, dd, J=4.1, 2.0 Hz), 8.05 (1H, dd, J=8.2, 2.0 Hz), 7.59 (1H, d, J=2.3 Hz), 7.31 (1H, dd, J=8.3, 4.2 Hz), 5.69-5.74 (1H, m), 3.70-3.78 (6H, m), 2.90-3.03 (4H, m), 2.43-2.48 (3H, m), 2.30-2.40 (1H, m), 1.54-1.59 (4H, m), 1.45-1.53 (4H, m), 1.12-1.17 (2H, m). Mass Spectrum (ESI) m/e=416.2 (M+1).

Workup

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

Sources & evidence

ORD record
ord-9d9141e5133349b19e4a0cf89655ef56
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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