Triethylsilane → HCID 11417583, compound

HRID 1792159Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[C:10]([CH3:14])[NH:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[SiH](CC)(CC)CC>C(Cl)Cl>[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][C:9]2[C:8]3[C:12](=[CH:13][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[NH:11][C:10]=2[CH3:14])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 6-methanesulfonyl-2-methyl-1H-indole (112 mg), prepared as described in Example 1 Step 3, in 9 ml CH2Cl2 was treated with p-bromo-benzaldehyde (100 mg) and 0.2 ml TMS-OTf. After cooling to 0° C., 0.26 ml of Et3SiH was added. The solution was stirred for 30 minutes followed by partitioning between EtOAc and water. Purification by TLC (2:1 hexane/EtOAc) gave 130 mg of 3-(4-bromo-benzyl)-6-methanesulfonyl-2-methyl-1H-indole 201, MS: 379 ([M+H]+).

Workup

customby partitioning between EtOAc and water
customPurification by TLC (2:1 hexane/EtOAc)

Sources & evidence

ORD record: ord-75e9fdcbd15d450b90e60bf40947cf41
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074939B2

Reaction notes

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