Ethyl 7-(4-(6-bromopyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate → Ethyl 7-(4-(6-tert-butylpyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate

HRID 1626462Notes

Reaction equation

HRID 1626462 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[CH:33]=[CH:32][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][C:17]=3[Cl:31])=[CH:13][CH:12]=2)=[O:10])[CH:5]=[CH:4][CH:3]=1.[Br-].[C:35]([Zn+])([CH3:38])([CH3:37])[CH3:36]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:35]([C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][C:17]=3[Cl:31])=[CH:32][CH:33]=2)=[O:10])[CH:5]=[CH:4][CH:3]=1)([CH3:38])([CH3:37])[CH3:36]

Participants

4

Reactant 2

HCID 86664393Ethyl 7-(4-(6-bromopyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylateHCID 178455669HCID 178455669, compound

Product 1

HCID 67288407Ethyl 7-(4-(6-tert-butylpyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Ethyl 7-(4-(6-bromopyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (Example 52, Step A; 30 mg, 0.056 mmol) and bis(tri-t-butylphosphine)palladium (0) (14 mg, 0.028 mmol) were diluted with tert-butylzinc bromide (113 μl, 0.056 mmol) and stirred for 1 hour. The reaction was loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 70% ethyl acetate/hexanes to yield the desired compound (8 mg, 0.016 mmol, 56% yield).

Workup

  1. washeluted with 5% ethyl acetate/hexanes to 70% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-50222428b0c14a56b7f4e088f5969142
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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