Potassium Carbonate → HCID 57958804, compound

HRID 1774127Notes

Reaction equation

HRID 1774127 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[N:6]=[C:5]2[NH:21][CH2:22][C:23]([F:26])([F:25])[F:24].C(=O)([O-])[O-].[K+].[K+].[F:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][NH:12][C:7]2[N:6]=[C:5]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:37]4[CH:38]=[CH:39][C:34]([F:33])=[CH:35][CH:36]=4)[CH:3]=3)[N:8]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 69012762HCID 69012762, compound

Product 1

HCID 57958804HCID 57958804, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 6-Bromo-N2-(4-fluoro-benzyl)-N4-(2,2,2-trifluoro-ethyl)-quinazoline-2,4-diamine (34 mg, 0.08 mmol), potassium carbonate (0.4M. 0.4 ml)), tetrakis(triphenylphosphine) palladium (10 mg) and 4-fluorophenyl boronic acid in DMF (1 ml) was heated to 170° C. for 5 minutes by microwave. The residue was purified by RP HPLC, eluting with 0.1% TFA-acetonitrile, to provide the desired product (20 mg). The product was characterized as follows: MS (m/z): 445 ([M+H]+, 100); HPLC Rt=3.10 minutes (Method A).

Workup

  1. customThe residue was purified by RP HPLC
  2. washeluting with 0.1% TFA-acetonitrile

Sources & evidence

ORD record
ord-d6c63334b6a0456897882d9857938458
Source dataset
uspto-grants-2016_02
Patent number
US09259426B2

Reaction notes

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