Sodium Carbonate → HCID 136348496, compound

HRID 510451Notes

Reaction equation

HRID 510451 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Cl[C:8]1[N:13]2[N:14]=[CH:15][C:16]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[C:19]=3[CH3:28])=[C:12]2[N:11]=[C:10]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:9]=1.[NH:35]1[CH:39]=[C:38](B(O)O)[CH:37]=[N:36]1>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:28][C:19]1[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][C:16]1[CH:15]=[N:14][N:13]2[C:8]([C:38]3[CH:39]=[N:35][NH:36][CH:37]=3)=[CH:9][C:10]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[N:11][C:12]=12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 177502781H-Pyrazole-4-boronic acidHCID 71527716HCID 71527716, compound

Product 1

HCID 136348496HCID 136348496, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

In a microwave vial was added Na2CO3 (0.049 mL, 0.097 mmol) was added to a suspension of 7-chloro-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-5-(4-morpholinyl)pyrazolo[1,5-a]pyrimidine (20 mg, 0.049 mmol), 1H-pyrazol-4-ylboronic acid (10.89 mg, 0.097 mmol), and PdCl2(dppf) (3.56 mg, 4.87 μmol) in 1,4-Dioxane (0.6 mL). The reaction mixture was purged with N2, sealed and irradiated with microwave at 150 C for 3 min (temp didn't reach to 150 C until at 7-8 min, total reaction time 10 min). LCMS showed complete reaction. The reaction mixture was concentrated, and the residue was loaded on a biotage column (10 g), which was eluted with 0-6% MeOH in DCM to give 17 mg (75%) of the product as a light brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.51 (s, 3H), 3.72 (m, 4H), 3.87 (m, 4H), 4.11 (s, 2H), 6.60 (s, 1H), 7.21 (t, 1H), 7.52 (t, 2H), 7.75 (s, 1H), 8.67 (s, 2H); LC/MS: MS (ES+) m/e 443.2 [M+H]+.

Workup

  1. customThe reaction mixture was purged with N2
  2. customsealed
  3. customirradiated with microwave at 150 C for 3 min (temp didn't reach to 150 C until at 7-8 min, total reaction time 10 min)
  4. customreaction
  5. concentrationThe reaction mixture was concentrated
  6. washwas eluted with 0-6% MeOH in DCM

Sources & evidence

ORD record
ord-5424598a318c4a48bb0be3ce74466159
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

Loading…