Lithium Hexamethyldisilazide → HCID 178432002, compound

HRID 589717Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]4[NH:24][N:23]=[N:22][N:21]=4)[CH:15]=3)(=[O:12])=[O:11])=[C:7]([CH3:25])[C:6]=2[CH:26]=1.[Li+].C[Si]([N-:32][Si](C)(C)C)(C)C>>[NH2:32][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]4[NH:24][N:23]=[N:22][N:21]=4)[CH:15]=3)(=[O:12])=[O:11])=[C:7]([CH3:25])[C:6]=2[CH:26]=1

Participants

Reactant 2

HCID 2733832Lithium Hexamethyldisilazide

HCID 178431997HCID 178431997, compound

Product 1

HCID 178432002HCID 178432002, compoundYield 2%

Procedure

The product was prepared from 5-bromo-3-methyl-N-[3-(1H-tetrazol-5-yl)phenyl]-1-benzothiophene-2-sulfonamide (Example 34) (45 mg, 0.1 mmol) and LiHMDS (1M in THF, 120 μL, 0.12 mmol) according to the General Procedure 4, described in Example 45, using a modified reaction time (130° C., 300 s, microwave reactor). The title compound was obtained in 2% yield (0.6 mg). MS (ESI+) calcd for C16H14N6O2S2 386.061965, found 386.061875.

Workup

customa modified reaction time (130° C., 300 s, microwave reactor)

Sources & evidence

ORD record: ord-c09792cf1e5c4ce8a33cb050703ebade
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233946B2

Reaction notes

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