Diisopropylamine → HCID 22632932, compound

HRID 2416779Notes

Reaction equation

[Li]CCCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[F:21])[NH2:17].F[C:23]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:24]=1[C:25]([OH:27])=[O:26]>>[Cl:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[F:21])[NH:17][C:23]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:24]=1[C:25]([OH:27])=[O:26]

Participants

Reactant 4

HCID 7912Diisopropylamine

HCID 97083-Chloro-4-fluoroaniline

HCID 5211702,4,5-Trifluorobenzoic acid

HCID 178418339Butyllithium

Product 1

HCID 22632932HCID 22632932, compoundYield 84.2%

Procedure

Using General Method 1, the reaction of 2.5 M solution of n-BuLi in hexanes (21 mL, 53 mmol), diisopropylamine (7.2 mL, 51 mmol), 3-chloro-4-fluoro-aniline (2.48 mL, 17 mmol), and 2,4,5-trifluorobenzoic acid (3.0 g, 17 mmol) provided 4.32 g of the crude title compound.

Sources & evidence

ORD record: ord-88603b8e98c940cda3298427a7040a3b
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825199B2

Reaction notes

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