Lithium Hexamethyldisilazide → HCID 66799791, compound

HRID 589715Notes

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:22]=[CH:23][CH:24]=3)[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[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:15]=[C:16]([CH:22]=[CH:23][CH:24]=3)[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:25])[C:6]=2[CH:26]=1

Participants

Reactant 2

HCID 2733832Lithium Hexamethyldisilazide

HCID 66799887HCID 66799887, compound2×

Product 1

HCID 66799791HCID 66799791, compoundYield 18.7%

Procedure

The intermediate ethyl 3-{[(5-amino-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate was prepared from ethyl 3-{[(5-bromo-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate (Intermediate 18) (45 mg, 0.1 mmol) and LiHMDS (1M in THF, 120 μL, 0.12 mmol) according to General Procedure 4, described in Example 45, using a modified reaction time and reaction temperature (100° C., 1500 s, microwave reactor) yielding 7.3 mg of ethyl 3-{[(5-amino-3-methyl-1-benzothien-2-yl)sulfonyl]-amino}benzoate.

Workup

customa modified reaction time and reaction temperature (100° C., 1500 s, microwave reactor)

Sources & evidence

ORD record: ord-e9c3c9d732ed4682822fe10677b61c09
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233946B2

Reaction notes

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