Dichloromethane → HCID 54588256, compound

HRID 389941Notes

Reaction equation

HRID 389941 reaction equation
[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15](Br)[CH:16]=2)[C:11](=[O:19])[NH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.ClCCl.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O.C(COC)OC>[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:23]3[CH:24]=[CH:25][N:20]=[CH:21][CH:22]=3)[CH:16]=2)[C:11](=[O:19])[NH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 12366387HCID 12366387, compound

Product 1

HCID 54588256HCID 54588256, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of EXAMPLE 1E (75 mg, 0.24 mmol), pyridin-4-ylboronic acid (44 mg, 0.36 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II)aaduct with dichloromethane (19.4 mg, 0.024 mmol) and potassium carbonate (66 mg, 0.48 mmol) in a mixture of 7:3:2 dimethoxyethane:water:ethanol (3 mL) was heated in a Biotage Initiator microwave at 150° C. for 20 minutes. The volatiles were removed, and the residue was purified by HPLC (Zorbax C-18, 0-100% gradient acetonitrile in water containing 0.1% trifluoroacetic acid) to yield the title compound. MS (ESI) m/z 314 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ 4.44 (s, 2H), 7.20 (d, J=7.14 Hz, 1H), 7.27-7.33 (m, 2H), 7.34-7.40 (m, 2H), 7.95 (d, J=6.35 Hz, 2H), 8.22-8.28 (m, 1H), 8.32-8.41 (m, 2H), 8.78-8.84 (m, 2H), 12.68 (br s, 1H).

Workup

  1. customThe volatiles were removed
  2. customthe residue was purified by HPLC (Zorbax C-18, 0-100% gradient acetonitrile in water containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-c8edd9ccc2d84c878ed30511d5402288
Source dataset
uspto-grants-2013_02
Patent number
US08383623B2

Reaction notes

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