Sodium t-butoxide → HCID 67284884, compound

HRID 1618777Notes

Reaction equation

HRID 1618777 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:13]=[N:14][CH:15]=[C:16]([F:18])[CH:17]=2)[C:3]=1[CH3:19].[CH3:20][C:21]1([CH3:36])[C:25]2=[N:26][CH:27]=[C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[CH:29]=[C:24]2[NH:23][CH2:22]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:21]1([CH3:36])[C:25]2=[N:26][CH:27]=[C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[CH:29]=[C:24]2[N:23]([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:13]=[N:14][CH:15]=[C:16]([F:18])[CH:17]=3)[C:3]=2[CH3:19])[CH2:22]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 67285530HCID 67285530, compound

Product 1

HCID 67284884HCID 67284884, compound

Reagents, catalysts & solvents 2

HCID 54751079XPhos PalladacycleCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to procedure Y using 4-chloro-2-(5-fluoropyridin-3-yl)-3-methyl-1,8-naphthyridine (15 mg, 0.055 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine (12.79 mg, 0.055 mmol), sodium tert-butoxide (10.53 mg, 0.110 mmol) and XPhos precatalyst (4.03 mg, 5.48 μmol) in toluene (4 mL) at 110° C. for 2 h. Purification by reverse phase HPLC gave 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-2-(5-fluoro-3-pyridinyl)-3-methyl-1,8-naphthyridine. 1H NMR (400 MHz, chloroform-d) δ ppm 9.17 (1H, dd, J=4.1, 2.0 Hz), 8.78 (1H, t, J=1.7 Hz), 8.61 (1H, d, J=2.7 Hz), 8.18 (1H, dd, J=8.4, 2.0 Hz), 7.91 (1H, ddd, J=9.0, 2.9, 1.8 Hz), 7.68 (1H, d, J=2.3 Hz), 7.50 (1H, dd, J=8.4, 4.3 Hz), 5.84 (1H, d, J=2.3 Hz), 3.84-3.94 (2H, m), 3.73-3.80 (4H, m), 3.01 (4H, td, J=4.9, 2.3 Hz), 2.41 (3H, s), 1.63 (3H, s), 1.58 (3H, s). Mass Spectrum (ESI) m/e=471.2 (M+1).

Workup

  1. customPrepared
  2. customat 110° C.
  3. customfor 2 h
  4. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-a16ff5eb084f497d94954e0a5dbb2927
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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