Sodium Carbonate → 3-chloro-N-[6-methyl-3-(3-methylphenyl)-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide

HRID 573684Notes

Reaction equation

HRID 573684 reaction equation
Br[C:2]1[S:22][C:5]2=[N:6][C:7]([CH3:21])=[CH:8][C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)(=[O:13])=[O:12])=[C:4]2[C:3]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=1.O(C([N:37]1[CH:41]=[C:40](B(O)O)[CH:39]=[N:38]1)=O)C(C)(C)C.C(=O)([O-])[O-].[Na+].[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>[Cl:20][C:16]1[CH:15]=[C:14]([S:11]([NH:10][C:9]2[CH:8]=[C:7]([CH3:21])[N:6]=[C:5]3[S:22][C:2]([C:40]4[CH:41]=[N:37][NH:38][CH:39]=4)=[C:3]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=4)[C:4]=23)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 441186751-tert-Butoxycarbonyl-1H-pyrazole-4-boronic acidHCID 68323728N-[2-bromo-6-methyl-3-(3-methylphenyl)thieno[2,3-b]pyridin-4-yl]-3-chlorobenzenesulfonamide

Product 1

HCID 683239123-chloro-N-[6-methyl-3-(3-methylphenyl)-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

A suspension of N-[2-bromo-6-methyl-3-(3-methylphenyl)thieno[2,3-b]pyridin-4-yl]-3-chlorobenzenesulfonamide (Description 60) (214 mg, 0.421 mmol), 1-tert-butoxylcarbonyl-1H-pyrazole-4-boronic acid, pinacol ester (124 mg, 0.421 mmol), tetrakis(triphenylphosphine)palladium(0) (48.7 mg, 0.042 mmol) and aqueous sodium carbonate (2M) (0.421 mL, 0.843 mmol) was degassed under a nitrogen atmosphere for ca. 10 min before being subjected to microwave heating at 120° C. for 30 min. The reaction mixture was then partitioned between ethyl acetate and water (ca. 30 mL each). The aqueous layer was separated and re-extracted with ethyl acetate (ca. 25 mL) and the combined organic layer passed through a phase separator and the solvent removed in vacuo. Purification by chromatography on silica, eluting with a gradient of 0-80% ethyl acetate in cyclohexane, afforded the title compound (75 mg). LCMS (A) m/z: 495 [M+1]+, Rt 1.31 min (acidic).

Workup

  1. customwas degassed under a nitrogen atmosphere for ca. 10 min
  2. customThe reaction mixture was then partitioned between ethyl acetate and water (ca. 30 mL each)
  3. customThe aqueous layer was separated
  4. extractionre-extracted with ethyl acetate (ca. 25 mL)
  5. customthe solvent removed in vacuo
  6. customPurification by chromatography on silica
  7. washeluting with a gradient of 0-80% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-438bc8b6eea449f49fcb690ad9107557
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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