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

HRID 1695807Notes

Reaction equation

HRID 1695807 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]([N:42]([CH2:45][CH3:46])[CH2:43][CH3:44])(=[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>[CH2:45]([N:42]([CH2:43][CH3:44])[S:39]([C:35]1[CH:34]=[C:33]([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:38]=[N:37][CH:36]=1)(=[O:40])=[O:41])[CH3:46]

Participants

5

Reactant 2

HCID 198548155-Bromo-N,N-diethylpyridine-3-sulfonamideHCID 582558202-Methyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide

Product 1

HCID 44539826N-(6-{5-[(Diethylamino)sulfonyl]-3-pyridinyl}-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamideYield 31%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

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 a microwave vial with Pd(PPh3)4 (10 mg) and 5-bromo-N,N-diethyl-3-pyridinesulfonamide (29 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). The residue obtained was further purified on silica, eluting with 0-100% EtOAc/cyclohexane over 15 min followed by 0-20% MeOH/DCM, to give the title compound (13 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)
  6. customThe residue obtained
  7. customwas further purified on silica
  8. washeluting with 0-100% EtOAc/cyclohexane over 15 min

Sources & evidence

ORD record
ord-cab5340718144a2895ba8cedcb245203
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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