Lithium Hexamethyldisilazide → HCID 66799911, compound

HRID 589719Notes

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:15]=[C:16]([CH:21]=[CH:22][CH:23]=3)[C:17]([O:19][CH3:20])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:24])[C:6]=2[CH:25]=1.[Li+].C[Si]([N-:31][Si](C)(C)C)(C)C>>[NH2:31][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=3)[C:17]([O:19][CH3:20])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:24])[C:6]=2[CH:25]=1

Participants

Reactant 2

HCID 2733832Lithium Hexamethyldisilazide

HCID 66799823HCID 66799823, compound

Product 1

HCID 66799911HCID 66799911, compoundYield 37.2%

Procedure

The intermediate methyl 3-{[(5-amino-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate was prepared from methyl 3-{[(5-bromo-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate (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 experiment was repeated four times giving 14 mg of methyl 3-{[(5-amino-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate.

Workup

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

Sources & evidence

ORD record: ord-4fd8d1a434a84d2eb14f69ac34a9af8b
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233946B2

Reaction notes

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