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5-Bromo-N-methylpyridine-3-sulfonamide → HCID 44539624, compound

HRID 1695806
Notes
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Reaction equation

HRID 1695806 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:9][C:10]2[CH:18]=[C:17]([Sn](C)(C)C)[CH:16]=[C:15]3[C:11]=2[CH:12]=[N:13][N:14]3S(C2C=CC=CC=2)(=O)=O)=[O:8])[N:6]=1.Br[C:33]1[CH:34]=[C:35]([S:39]([NH:42][CH3:43])(=[O:41])=[O:40])[CH:36]=[N:37][CH:38]=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.CN(C=O)C>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:9][C:10]2[CH:18]=[C:17]([C:33]3[CH:38]=[N:37][CH:36]=[C:35]([S:39]([NH:42][CH3:43])(=[O:40])=[O:41])[CH:34]=3)[CH:16]=[C:15]3[C:11]=2[CH:12]=[N:13][NH:14]3)=[O:8])[N:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 467389795-Bromo-N-methylpyridine-3-sulfonamideHCID 582558202-Methyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide

Product 1

HCID 44539624HCID 44539624, compoundYield 3.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
120 °C

Procedure

2-Methyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide (50 mg) was placed in microwave vial with Pd(PPh3)4 (10 mg) and 5-bromo-N-methyl-3-pyridinesulfonamide (24.6 mg) was added. DMF (2 ml) was added and the reaction was heated under microwave irradiation for 15 min at 120° C. The reaction was evaporated to dryness and the residue was dissolved in IPA (2 ml) and 2M NaOH (aq) (1 ml). The reaction was stirred at RT for 3 h then evaporated to dryness. The residue was purified by MDAP (method E) to give the title compound (1.5 mg).

Workup

  1. additionwas added
  2. customThe reaction was evaporated to dryness
  3. dissolutionthe residue was dissolved in IPA (2 ml)
  4. customthen evaporated to dryness
  5. customThe residue was purified by MDAP (method E)

Sources & evidence

ORD record
ord-80b0e61404ba4d6d92bc24342b6810ce
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163743B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes