Benzenesulfonyl chloride → HCID 68545398, compound

HRID 2245503Notes

Reaction equation

HRID 2245503 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([C:15]1[CH:31]=[CH:30][C:18]([CH2:19][N:20]2[C:28]3[C:23](=[CH:24][C:25]([NH2:29])=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].C(N(C(C)C)CC)(C)C.CCCCCC>C(Cl)Cl.CCOC(C)=O>[C:11]([C:15]1[CH:31]=[CH:30][C:18]([CH2:19][N:20]2[C:28]3[C:23](=[CH:24][C:25]([NH:29][S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)=[CH:17][CH:16]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8058HexaneHCID 81531DiisopropylethylamineHCID 43165373HCID 43165373, compound

Product 1

HCID 68545398HCID 68545398, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Benzenesulfonyl chloride (0.56 g, 3.12 mmol) was added in one portion to 1-(4-tert-butylbenzyl)-5-amino-1H-indole (0.84 g, 3.02 mmol) and diisopropylethylamine (0.43 g, 3.17 mmol) in CH2Cl2 (20 ml) at 0° C. under a nitrogen atmosphere. The resulting yellow solution was stirred at 0° C. for 5 minutes and then at room temperature for 2 hours. The reaction was quenched with water (2 ml) and then concentrated in vacuo to a brown powder. The powder was partitioned between EtOAc (15 ml) and std NaHCO3 (10 ml). All organics were combined, extracted with water (10 ml) and brine (10 ml), dried with MgSO4, filtered and concentrated in vacuo to a brown powder. Gradient SiO2 chromatography (Hexane:EtOAc) afforded N-[1-(4-tert-butyl-benzyl)-1H-indol-5-yl]-benzenesulfonamide as a brown powder (1.18 g, 94% yield): MS (ESI) m/z 419, MS (ESI) m/z 417.

Workup

  1. waitat room temperature for 2 hours
  2. customThe reaction was quenched with water (2 ml)
  3. concentrationconcentrated in vacuo to a brown powder
  4. customThe powder was partitioned between EtOAc (15 ml) and std NaHCO3 (10 ml)
  5. extractionextracted with water (10 ml) and brine (10 ml)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to a brown powder

Sources & evidence

ORD record
ord-5b2a1bca0a7f4f79bf4e05d2f6569152
Source dataset
uspto-grants-2010_03
Patent number
US07683091B2

Reaction notes

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