Dichloromethane → HCID 56963505, compound

HRID 403280Notes

Reaction equation

HRID 403280 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12]([N:14]1[CH2:17][CH:16]([NH:18][C@H:19]3[CH2:23][CH2:22][N:21]([C:24]([C:26]4[S:27][CH:28]=[CH:29][N:30]=4)=[O:25])[CH2:20]3)[CH2:15]1)=[O:13])[CH2:6][CH2:5]2.[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:31]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH2:8][N:7]([C:12]([N:14]2[CH2:15][CH:16]([NH:18][C@H:19]4[CH2:23][CH2:22][N:21]([C:24]([C:26]5[S:27][CH:28]=[CH:29][N:30]=5)=[O:25])[CH2:20]4)[CH2:17]2)=[O:13])[CH2:6][CH2:5]3)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 56963504HCID 56963504, compound

Product 1

HCID 56963505HCID 56963505, compoundYield 86%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of compound 10 (82 mg, 0.167 mmol), phenyl boronic acid 2a (35 mg, 0.284 mmol), Pd(dppf)Cl2.CH2Cl2 (14 mg, 0.0167 mmol) and Na2CO3 (35 mg, 0.334 mmol) in dioxane (0.8 mL) and water (0.2 mL) in a capped vial was heated at 80° C. for 6 h. The reaction mixture was diluted with EtOAc and water. The organic layer was concentrated and purified by chromatography (silica gel, 5% MeOH/EtOAc) to give compound 11 (70 mg). MS m/z (M+H+) 488.

Workup

  1. concentrationThe organic layer was concentrated
  2. custompurified by chromatography (silica gel, 5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-762b156e1dcc4255832d7ececec8ce45
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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