Dichloromethane → HCID 57975029, compound

HRID 1865117Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:24])[C:8]([CH2:22][CH3:23])=[C:9]([C:20]#[N:21])[C:10]=1B1OC(C)(C)C(C)(C)O1)=[O:5])[CH3:2].Br[C:26]1[CH:41]=[CH:40][CH:39]=[CH:38][C:27]=1[O:28][CH2:29][CH2:30][NH:31][S:32]([CH:35]([CH3:37])[CH3:36])(=[O:34])=[O:33].C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:24])[C:8]([CH2:22][CH3:23])=[C:9]([C:20]#[N:21])[C:10]=1[C:40]1[CH:41]=[CH:26][C:27]([O:28][CH2:29][CH2:30][NH:31][S:32]([CH:35]([CH3:37])[CH3:36])(=[O:33])=[O:34])=[CH:38][CH:39]=1)=[O:5])[CH3:2]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 10340Sodium Carbonate

HCID 579748024-cyano-5-ethyl-1-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid ethyl ester

HCID 69061091HCID 69061091, compound

Product 1

HCID 57975029HCID 57975029, compoundYield 99.2%

Procedure

Prepare the title compound in a manner analogous to the procedure set forth in Example E-281, using 4-cyano-5-ethyl-1-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid ethyl ester (478 mg, 1.4 mmol, prepared in preparation 50), N-[2-(bromo-phenoxy)-ethyl]-i-propanesulfonamide (385 mg, 1.2 mmol, prepared in preparation 82), aqueous sodium carbonate (3.0 mL, 6.0 mmol, 2N), and [1,1′-bis(diphenyl-phosphino)-ferrocene]dichloropalladium(II) complex with methylene chloride (1:1) (30 mg, 0.04 mmol) to give 533 mg (99%) of the title compound. Mass spectrum (ES+)=446.1 (M−1).

Sources & evidence

ORD record: ord-5b566d3f9d3f4e9b9bd9bfc6d1c908f9
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625932B2

Reaction notes

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