Sodium Carbonate → 1-(6-fluoro-2-methoxypyridin-3-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide

HRID 1473617Notes

Reaction equation

HRID 1473617 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[F:7][C:8]1[N:13]=[C:12]([O:14][CH3:15])[C:11](B(O)O)=[CH:10][CH:9]=1.Cl[C:20]1[C:29]2[C:24](=[CH:25][C:26]([S:30]([NH:33][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][N:35]=3)(=[O:32])=[O:31])=[CH:27][CH:28]=2)[CH:23]=[CH:22][N:21]=1>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>[F:7][C:8]1[N:13]=[C:12]([O:14][CH3:15])[C:11]([C:20]2[C:29]3[C:24](=[CH:25][C:26]([S:30]([NH:33][C:34]4[CH:39]=[CH:38][N:37]=[CH:36][N:35]=4)(=[O:31])=[O:32])=[CH:27][CH:28]=3)[CH:23]=[CH:22][N:21]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 866876591-chloro-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamideHCID 86687685(6-Fluoro-2-methoxypyridin-3-yl)boronic acid

Product 1

HCID 866876841-(6-fluoro-2-methoxypyridin-3-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamideYield 40%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a microwave vial containing Na2CO3 (1.216 ml, 2.432 mmol), (6-fluoro-2-methoxypyridin-3-yl)boronic acid (0.166 g, 0.973 mmol) and 1-chloro-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (0.26 g, 0.811 mmol) and Dioxane (4.05 ml) was added tetrakis(triphenylphosphine)palladium (0.094 g, 0.081 mmol) and purged with nitrogen and irradiated at 100° C. for 30 min. The reaction mixture was diluted with DMSO to dissolve the observed yellow ppt. Purification was done on reverse phase HPLC with 0.1% NH4OH in ACN and water as mobile phase to obtain 1-(6-fluoro-2-methoxypyridin-3-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (133.2 mg, 0.324 mmol, 39.9% yield) as yellow solid; m/z (ESI) 412.0 (M+H)+.

Workup

  1. custompurged with nitrogen
  2. customirradiated at 100° C. for 30 min
  3. additionThe reaction mixture was diluted with DMSO
  4. dissolutionto dissolve the observed yellow ppt
  5. customPurification

Sources & evidence

ORD record
ord-8fd4ad227c934c2bb8be3f7026c74943
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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