Potassium Phosphate, Tribasic → HCID 86710625, compound

HRID 1027222Notes

Reaction equation

HRID 1027222 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]([CH3:19])[CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)=[CH:4][CH:3]=1.[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[C:22]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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+].C1COCC1.O>[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[C:22]=1[C:4]1[CH:3]=[CH:2][N:7]=[N:6][C:5]=1[N:8]([CH3:19])[CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 3294524(2-Fluoro-6-methoxyphenyl)boronic acidHCID 867105396-chloro-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine

Product 1

HCID 86710625HCID 86710625, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 54751079XPhos PalladacycleCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Intermediate 1-1 (2.83 g, 10.0 mmol), (2-fluoro-6-methoxyphenyl)boronic acid, and K3PO4 (5.52 g, 26.0 mmol) were added to a microwave vial. 2nd Generation XPhos Precatalyst (0.32 g, 0.40 mmol) was then added to the mixture followed by addition of 1:1 THF/water (50 mL). The reaction mixture was sealed and stirred at RT for 4 h then extracted with CH2Cl2 (2×). The crude material was purified by catch and release using SiliaBond Propylsulfonic Acid® (3 eq, MeOH as eluent and a 2 N ammonia solution in MeOH to release the material). The solvent was concentrated in vacuo to afford the title compound as a brown gel (2.87 g, 77%). [M+H]: 373.4; 1H NMR (400 MHz, DMSO) δ 7.43 (td, J=8.5, 7.0 Hz, 1H), 7.36 (d, J=9.5 Hz, 1H), 7.08 (d, J=9.5 Hz, 1H), 6.98 (d, J=8.5 Hz, 1H), 6.92 (td, J=8.5, 1.0 Hz, 1H), 5.07 (bs, 1H), 3.74 (s, 3H), 3.31 (s, 3H), 1.47-1.55 (m, 2H), 1.33-1.48 (m, 2H), 1.24 (s, 6H), 1.09 (s, 6H).

Workup

  1. customThe reaction mixture was sealed
  2. extractionthen extracted with CH2Cl2 (2×)
  3. customThe crude material was purified by catch and release
  4. concentrationThe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-24126b79600a4305bb140c33f19374bb
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

Loading…