Potassium Carbonate → HCID 89815922, compound

HRID 1483006Notes

Reaction equation

HRID 1483006 reaction equation
Br[C:2]1[C:3]([C:32]([F:35])([F:34])[F:33])=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]3[C:14]4[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[C:18]([C:25]([O:27][CH3:28])=[O:26])=[CH:17][C:15]=4[N:16]=[C:10]3[C@H:9]2[CH:29]([CH3:31])[CH3:30])=[N:6][CH:7]=1.[C:36]([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[CH:29]([C@H:9]1[N:8]([C:5]2[N:4]=[C:3]([C:32]([F:35])([F:33])[F:34])[C:2]([CH3:36])=[CH:7][N:6]=2)[CH2:13][CH2:12][N:11]2[C:14]3[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[C:18]([C:25]([O:27][CH3:28])=[O:26])=[CH:17][C:15]=3[N:16]=[C:10]12)([CH3:31])[CH3:30]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 89816039HCID 89816039, compound

Product 1

HCID 89815922HCID 89815922, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (R)-methyl 2-(5-bromo-4-(trifluoromethyl)pyrimidin-2-yl)-1-isopropyl-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate (7 mg, 0.012 mmol), Pd(PPh3)4 (1 mg, cat. Amount), 2M aq. K2CO3 solution (100 μL, excess), and dry 1,4-Dioxane (700 μL) was degassed and refilled with nitrogen gas for 3 times. A solution of 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (5 mg, excess) in dry 1,4-Dioxane (100 μL) was added. The mixture was heated in a microwave oven for 30 minutes at 120° C. After concentration, the residue was filtered and purified by Gilson to afford 3.5 mg (R)-methyl 1-isopropyl-2-(5-methyl-4-(trifluoromethyl)pyrimidin-2-yl)-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate (56% yield). LC-MS: m/z 512.3 [M+H]+.

Workup

  1. customwas degassed
  2. additionrefilled with nitrogen gas for 3 times
  3. additionA solution of 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (5 mg, excess) in dry 1,4-Dioxane (100 μL) was added
  4. concentrationAfter concentration
  5. filtrationthe residue was filtered
  6. custompurified by Gilson

Sources & evidence

ORD record
ord-a62414a375ff4b5db1e9c3fa98977795
Source dataset
uspto-grants-2016_08
Patent number
US09416135B2

Reaction notes

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