Pyridine → HCID 58696159, compound

HRID 1674700Notes

Reaction equation

HRID 1674700 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)[CH:5]=[CH:4][C:3]=1[NH2:17].[Cl:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[S:26](Cl)(=[O:28])=[O:27].N1C=CC=CC=1>C(Cl)Cl>[Cl:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[S:26]([NH:17][C:3]1[CH:4]=[CH:5][C:6]([B:8]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH3:16])([CH3:15])[O:9]2)=[CH:7][C:2]=1[F:1])(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27342222,3-Dichlorobenzene-1-sulfonyl chlorideHCID 179061722-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 58696159HCID 58696159, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 25 was prepared in analogy to GP 4 from 1.78 g 2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (7.5 mmol) and 2.03 g 2,3-dichloro-benzenesulfonyl chloride (8.25 mmol, 1.1 eq.) in 20 mL DCM and in the presence of 0.66 mL pyridine (8.25 mmol, 1.1. eq.) yielding after trituration 2.42 g of the target compound (72% yield).

Sources & evidence

ORD record
ord-f9b4c3a0e70542e5b0254c45057dfeb2
Source dataset
uspto-grants-2011_08
Patent number
US08003655B2

Reaction notes

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