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Pyridine → Thiophene-2-sulfonic acid [5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-amide

HRID 25496
Notes
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Reaction equation

HRID 25496 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:19][CH3:20])=[C:16]([NH2:18])[CH:17]=1)=[CH:5]2.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[S:26](Cl)(=[O:28])=[O:27].N1C=CC=CC=1>O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:19][CH3:20])=[C:16]([NH:18][S:26]([C:22]3[S:21][CH:25]=[CH:24][CH:23]=3)(=[O:28])=[O:27])[CH:17]=1)=[CH:5]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 855182-Thiophenesulfonyl chlorideHCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine2×

Product 1

HCID 9910030Thiophene-2-sulfonic acid [5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

The product from Example 3, 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine, (0.274 g, 1.0 mmol) was mixed with thiophene-2-sulfonyl chloride (0.192 g, 1.0 mmol) and pyridine (3 mL) was added, and the reaction mixture was heated briefly to 50° C. and then allowed to stand overnight at room temperature. Water (7 mL) was added and the mixture allowed to stand 1.75 hours at room temperature. The mixture was partitioned between water (200 mL) and ethyl acetate (200 mL) and the organic layer was washed with 1N HCl (100 mL), water (100 mL), and brine (100 mL), dried (magnesium sulfate), filtered, and concentrated to a purple-tinted solid. The solid was triturated with hexanes/ethyl acetate, 1/1, v/v to give the product (0.322 g), mp 211-213° C.

Workup

  1. additionwas added
  2. waitto stand 1.75 hours at room temperature
  3. customThe mixture was partitioned between water (200 mL) and ethyl acetate (200 mL)
  4. washthe organic layer was washed with 1N HCl (100 mL), water (100 mL), and brine (100 mL)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated to a purple-tinted solid
  8. customThe solid was triturated with hexanes/ethyl acetate, 1/1, v/v

Sources & evidence

ORD record
ord-b974ad7baa4741b79bf348c0e9690f04
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06858739B2

Reaction notes

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