Dichloromethane → HCID 57974960, compound

HRID 1865118Notes

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:31]=[CH:30][C:29]([N:32]([CH3:42])[CH2:33][CH2:34][NH:35][S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])=[CH:28][CH:27]=1.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:26]1[CH:27]=[CH:28][C:29]([N:32]([CH3:42])[CH2:33][CH2:34][NH:35][S:36]([CH:39]([CH3:40])[CH3:41])(=[O:37])=[O:38])=[CH:30][CH:31]=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 57975225HCID 57975225, compound

Product 1

HCID 57974960HCID 57974960, compoundYield 55%

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 (817 mg, 2-4 mmol, prepared in preparation 50), propane-2-sulfonic acid {2-[(4-bromo-phenyl)-methyl-amino]-ethyl}-amide (550 mg, 1.6 mmol, prepared in preparation 81), aqueous sodium carbonate (4.0 mL, 8.0 mmol, 2N), and [1,1′-bis(diphenyl-phosphino)-ferrocene]dichloropalladium(II) complex with methylene chloride (1:1) (39 mg, 0.05 mmol) to give 404 mg (55%) of the title compound. Mass spectrum (ES+)=461.1 (M+1).

Sources & evidence

ORD record: ord-e4b0c57bd88b4699ae149a9e2ba7d60f
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625932B2

Reaction notes

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