Dichloromethane → HCID 68006699, compound

HRID 1053908Notes

Reaction equation

HRID 1053908 reaction equation
FC(F)(F)S(O[C:7]1[CH:11]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)[CH:10]([C:22]2[CH:27]=[CH:26][C:25]([N:28]3[C:32]([CH3:33])=[CH:31][CH:30]=[C:29]3[CH3:34])=[CH:24][CH:23]=2)[CH2:9][CH:8]=1)(=O)=O.CC1(C)C(C)(C)OB([C:45]2[CH:50]=[CH:49][C:48]([NH:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[CH:47][CH:46]=2)O1.C([O-])([O-])=O.[K+].[K+].ClCCl>O1CCOCC1.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:18]([C:15]1[CH:16]=[CH:17][C:12]([CH:11]2[C:7]([C:45]3[CH:46]=[CH:47][C:48]([NH:51][C:52](=[O:58])[O:53][C:54]([CH3:55])([CH3:56])[CH3:57])=[CH:49][CH:50]=3)=[CH:8][CH2:9][CH:10]2[C:22]2[CH:23]=[CH:24][C:25]([N:28]3[C:29]([CH3:34])=[CH:30][CH:31]=[C:32]3[CH3:33])=[CH:26][CH:27]=2)=[CH:13][CH:14]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2734617tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamateHCID 88548548HCID 88548548, compound

Product 1

HCID 68006699HCID 68006699, compoundYield 95.4%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 7J (373 mg, 0.721 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (253 mg, 0.793 mmol), K2CO3 (299 mg, 2.162 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (58.8 mg, 0.072 mmol) in 1,4-dioxane (4 mL) and water (1 mL) was heated at 100° C. for 16 hours. The mixture was concentrated in vacuo, the residue was purified by column chromatography (on silica gel, eluted with dichloromethane/petroleum ether=2:1, v/v) to afford the title compound (386 mg, 0.688 mmol, 95% yield) as a solid. LC/MS (ESI) m/z 561 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography (on silica gel
  3. washeluted with dichloromethane/petroleum ether=2:1

Sources & evidence

ORD record
ord-7af0e4a4e24f4b55a8b7a89d1498257c
Source dataset
uspto-grants-2016_07
Patent number
US09394279B2

Reaction notes

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