Sodium t-butoxide → HCID 67285151, compound

HRID 1618759Notes

Reaction equation

HRID 1618759 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:3]=1[CH3:19].[N:20]1([C:26]2[CH:31]=[C:30]3[NH:32][CH2:33][C:34]4([CH2:39][CH2:38][S:37](=[O:41])(=[O:40])[CH2:36][CH2:35]4)[C:29]3=[CH:28][CH:27]=2)[CH2:25][CH2:24][O:23][CH2:22][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+]>[F:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:32]3[C:30]4[C:29](=[CH:28][CH:27]=[C:26]([N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)[CH:31]=4)[C:34]4([CH2:39][CH2:38][S:37](=[O:40])(=[O:41])[CH2:36][CH2:35]4)[CH2:33]3)=[C:3]([CH3:19])[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 23676156Sodium t-butoxideHCID 596310754-Chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinolineHCID 67284671HCID 67284671, compound

Product 1

HCID 67285151HCID 67285151, compound

Reagents, catalysts & solvents 1

HCID 54751079XPhos PalladacycleCatalyst

Procedure

Prepared according to procedure Y using 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (29.6 mg, 0.109 mmol), 6-morpholin-4-yl-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-thiopyran]1′,1′-dioxide (35 mg, 0.109 mmol), sodium tert-butoxide (20.9 mg, 0.217 mmol) and XPhos precatalyst (8.02 mg, 10.86 μmol). Purification by reverse phase HPLC gave 1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-6-(4-morpholinyl)-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-thiopyran]1′,1′-dioxide. 1H NMR (400 MHz, chloroform-d) δ ppm 8.74 (1H, dt, J=4.9, 1.4 Hz), 7.82-7.96 (3H, m), 7.75 (1H, dd, J=9.2, 6.1 Hz), 7.39-7.44 (1H, m), 7.24-7.29 (1H, m), 7.19 (1H, d, J=8.2 Hz), 6.35 (1H, dd, J=8.2, 2.2 Hz), 5.61 (1H, d, J=2.2 Hz), 3.94-3.99 (1H, m), 3.87-3.92 (1H, m), 3.68-3.78 (4H, m), 3.07-3.26 (4H, m), 2.91-3.03 (4H, m), 2.61-2.76 (2H, m), 2.29-2.49 (5H, m). Mass Spectrum (ESI) m/e=559.0 (M+1)

Workup

  1. customPrepared
  2. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-81171a45779b4b278fbc05114e2cc7da
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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