Sodium Carbonate → HCID 73775730, compound

HRID 2207274Notes

Reaction equation

HRID 2207274 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]3[S:20][CH:21]=[CH:22][N:23]=3)(=[O:17])=[O:16])=[CH:11][C:10]=2[C:24]#[N:25])=[C:4]([C:26]2[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=2)[CH:3]=1.[F:32][C:33]1[C:38](B(O)O)=[CH:37][CH:36]=[CH:35][N:34]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O.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>[C:24]([C:10]1[CH:11]=[C:12]([S:15]([NH:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)(=[O:17])=[O:16])[CH:13]=[CH:14][C:9]=1[O:8][C:5]1[C:4]([C:26]2[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=2)=[CH:3][C:2]([C:38]2[C:33]([F:32])=[N:34][CH:35]=[CH:36][CH:37]=2)=[N:7][CH:6]=1)#[N:25]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 90100518HCID 90100518, compound

Product 1

HCID 73775730HCID 73775730, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

10 mg of 4-((6-chloro-4-(1-methyl-1H-pyrazol-5-yl)pyridin-3-yl)oxy)-3-cyano-N-(thiazol-2-yl)benzenesulfonamide was dissolved in DMF/H2O=1:1 (0.46 mL), and 3.2 mg of (2-fluoropyridin-3-yl)boronic acid, 0.8 mg of Pd(PPh3)4 and 7.4 mg of Na2CO3 were added thereto. After reacting with microwave reactor at 120° C. for 5 minutes, DMF was removed by concentrating under reduced pressure. After extracting with EA, the extract was treated with MgSO4 and concentrated under reduced pressure. The residue was separated by PLC (developing solvent, EA) to obtain 3.2 mg (28% yield) of the title compound.

Workup

  1. additionwere added
  2. customDMF was removed
  3. concentrationby concentrating under reduced pressure
  4. extractionAfter extracting with EA
  5. additionthe extract was treated with MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated by PLC (developing solvent, EA)

Sources & evidence

ORD record
ord-0e1bfe03d2b04a2f911e25fe7f49d8dc
Source dataset
uspto-grants-2016_06
Patent number
US09376429B2

Reaction notes

Loading…