5-Bromopyridine-3-sulfonamide → N-{6-[5-(Aminosulfonyl)-3-pyridinyl]-1H-indazol-4-yl}-2-methyl-1,3-thiazole-4-carboxamide

HRID 1695759Notes

Reaction equation

HRID 1695759 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:9][C:10]2[CH:18]=[C:17](B3OC(C)(C)C(C)(C)O3)[CH:16]=[C:15]3[C:11]=2[CH:12]=[N:13][NH:14]3)=[O:8])[N:6]=1.Br[C:29]1[CH:30]=[C:31]([S:35]([NH2:38])(=[O:37])=[O:36])[CH:32]=[N:33][CH:34]=1>CC(O)C.C(=O)(O)[O-].[Na+].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>[NH2:38][S:35]([C:31]1[CH:30]=[C:29]([C:17]2[CH:16]=[C:15]3[C:11]([CH:12]=[N:13][NH:14]3)=[C:10]([NH:9][C:7]([C:5]3[N:6]=[C:2]([CH3:1])[S:3][CH:4]=3)=[O:8])[CH:18]=2)[CH:34]=[N:33][CH:32]=1)(=[O:37])=[O:36]

Participants

6

Reactant 2

HCID 126842585-Bromopyridine-3-sulfonamideHCID 582557722-methyl-N-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide

Product 1

HCID 44540127N-{6-[5-(Aminosulfonyl)-3-pyridinyl]-1H-indazol-4-yl}-2-methyl-1,3-thiazole-4-carboxamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3776IsopropanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

2-Methyl-N-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide (23 mg, 0.06 mmol), 5-bromo-3-pyridinesulfonamide (18 mg, 0.078 mmol) and Pd(PPh3)4 (7 mg, 0.006 mmol) were combined in IPA (0.5 ml) and 1 M sodium bicarbonate (aq) (0.18 ml). The reaction was heated in a Biotage microwave at 120° C. for 10 mins. After cooling the solvent was removed under a stream of nitrogen and the solid partitioned between water (10 ml) and ethyl acetate:DCM (3×10 ml, 1:1, v/v). A few drops of brine were added to aid separation. The organic layers were combined, passed through a hydrophobic frit and dried under a stream of nitrogen. The residue was dissolved in MeOH:DMSO (0.5 ml, 1:1, v/v) and purified by MDAP (Method B). The solvent was removed under a stream of nitrogen to give the title compound, 1.5 mg.

Workup

  1. temperatureAfter cooling the solvent
  2. customwas removed under a stream of nitrogen
  3. customthe solid partitioned between water (10 ml) and ethyl acetate
  4. additionA few drops of brine were added
  5. customseparation
  6. customdried under a stream of nitrogen
  7. dissolutionThe residue was dissolved in MeOH
  8. customDMSO (0.5 ml, 1:1, v/v) and purified by MDAP (Method B)
  9. customThe solvent was removed under a stream of nitrogen

Sources & evidence

ORD record
ord-1dbb4a2979c64be980e21c12b0a9fb58
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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