Potassium Carbonate → HCID 136409069, compound

HRID 1473587Notes

Reaction equation

HRID 1473587 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([N:15]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[C:16]3[S:17][CH:18]=[CH:19][N:20]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Cl:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[C:33]([OH:40])[CH:32]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>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.O>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([S:12]([N:15]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[C:16]4[S:17][CH:18]=[CH:19][N:20]=4)(=[O:14])=[O:13])=[CH:9][CH:10]=3)[CH:5]=[CH:4][N:3]=2)=[C:33]([OH:40])[CH:32]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 67464855B-(4-Chloro-2-hydroxyphenyl)boronic acidHCID 866874151-Chloro-N-(4-methoxybenzyl)-N-(thiazol-2-YL)isoquinoline-6-sulfonamide

Product 1

HCID 136409069HCID 136409069, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

To a microwave vial charged with 1-chloro-N-(4-methoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (Intermediate JJJ) (80 mg, 0.179 mmol), (4-chloro-2-hydroxyphenyl)boronic acid (30.9 mg, 0.179 mmol), potassium carbonate (124 mg, 0.897 mmol) and Pd(Ph3P)4 (20.73 mg, 0.018 mmol) was added dioxane (897 μl) and Water (299 μl) and irradiated at 100° C. for 30 min affording conversion to desired product as the primary species. The organic layer was decanted, the aqueous rinsed with EtOAc and the combined organics dried under reduced pressure. m/z (ESI) 537.9 (M+H)+.

Workup

  1. customirradiated at 100° C. for 30 min

Sources & evidence

ORD record
ord-05836aa75d55459fafa926d4d9fa78cd
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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