Cesium fluoride → HCID 66701212, compound

HRID 2075529Notes

Reaction equation

HRID 2075529 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1Br)=[O:9])([CH3:6])[CH3:5].[Cl:22][C:23]1[CH:28]=[CH:27][C:26](/[CH:29]=[CH:30]/B(O)O)=[CH:25][CH:24]=1.[F-].[Cs+]>CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:21])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1/[CH:30]=[CH:29]/[C:26]1[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=1)=[O:9])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 642694trans-2-(4-Chlorophenyl)vinylboronic acidHCID 58370136HCID 58370136, compound

Product 1

HCID 66701212HCID 66701212, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Procedure

50 mg 2-[(1-bromo-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester, 49.5 mg tetrakis(triphenylphosphine)palladium (0), 28.7 mg trans-2-(4-chloro-phenyl) vinylboronic acid and 43 mg CsF were suspended in 1 ml of MeOH and 3 ml of dimethoxyethane, deoxygenated with Argon, and heated to 80° for 14h. The reaction was filtered, purified by RP-HPLC and freeze-dried to give 38 mg of 2-({1-[(E)-2-(4-Chloro-phenyl)-vinyl]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid methyl ester (65%).

Workup

  1. custom3 ml of dimethoxyethane, deoxygenated with Argon
  2. temperatureheated to 80° for 14h
  3. filtrationThe reaction was filtered
  4. custompurified by RP-HPLC
  5. customfreeze-dried

Sources & evidence

ORD record
ord-58b163068ae74f56b9a5a497bbac408f
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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