Potassium Carbonate → 5-(5-{[(1,1-Dimethylethyl)amino]sulfonyl}-2-thienyl)-1H-indole-7-carboxamide

HRID 656117Notes

Reaction equation

HRID 656117 reaction equation
Br[C:2]1[S:6][C:5]([S:7]([NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])=[O:8])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:23]2[CH:24]=[C:25]3[C:29](=[C:30]([C:32]([NH2:34])=[O:33])[CH:31]=2)[NH:28][CH:27]=[CH:26]3)O1.C(=O)([O-])[O-].[K+].[K+]>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>[CH3:12][C:11]([NH:10][S:7]([C:5]1[S:6][C:2]([C:23]2[CH:24]=[C:25]3[C:29](=[C:30]([C:32]([NH2:34])=[O:33])[CH:31]=2)[NH:28][CH:27]=[CH:26]3)=[CH:3][CH:4]=1)(=[O:9])=[O:8])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27571875-Bromo-N-tert-butylthiophene-2-sulfonamideHCID 593327405-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide

Product 1

HCID 593326025-(5-{[(1,1-Dimethylethyl)amino]sulfonyl}-2-thienyl)-1H-indole-7-carboxamideYield 59.1%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

5-bromo-N-(1,1-dimethylethyl)-2-thiophenesulfonamide (828 mg, 2.78 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (4.17 mmol, 1.5 eq), potassium carbonate (1.524 g) and Pd(PPh3)4 (50 mg) were heated in Microwave at 150 degree for 15 mins after degassing for 5 mins with argon. The reaction solution was filtered off palladium with PL-thiol MP SPE cartridge, concentrated and purified by HPLC with CH3CN/H2O/0.1% TFA to give 620 mg title compound.

Workup

  1. customafter degassing for 5 mins with argon
  2. filtrationThe reaction solution was filtered off palladium with PL-thiol MP SPE cartridge
  3. concentrationconcentrated
  4. custompurified by HPLC with CH3CN/H2O/0.1% TFA

Sources & evidence

ORD record
ord-50a947de4001411788e4511e18ae87ac
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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