Trifluoroacetic acid → HCID 46864596, compound

HRID 1803262Notes

Reaction equation

HRID 1803262 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:11]3[CH2:17][CH2:16][CH2:15][CH:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:12]=3[N:13]=2)=[CH:4][C:3]=1[O:24][CH3:25].[C:26]([OH:32])([C:28]([F:31])([F:30])[F:29])=[O:27].[CH3:33][C:34]1[CH:39]=[C:38](B(O)O)[CH:37]=[CH:36][N:35]=1.C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:29][C:28]([F:31])([F:30])[C:26]([OH:32])=[O:27].[CH3:25][O:24][C:3]1[CH:4]=[C:5]([NH:8][C:9]2[S:10][C:11]3[CH2:17][CH2:16][CH2:15][CH:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:12]=3[N:13]=2)[CH:6]=[CH:7][C:2]=1[C:38]1[CH:37]=[CH:36][N:35]=[C:34]([CH3:33])[CH:39]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 41926642-Methylpyridine-4-boronic acidHCID 86632611HCID 86632611, compound

Product 1

HCID 46864596HCID 46864596, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-(4-bromo-3-methoxyphenyl)-4-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-2-amine, TFA (70 mg, 0.13 mmol), 2-methylpyridin-4-ylboronic acid (36 mg, 0.26 mmol), tetrakis(triphenylphosphine)palladium(0) (7.6 mg, 6.6 μmol) and Cs2CO3 (172 mg, 0.529 mmol) in DME (994 μL)/water (328 μL) was heated at 100° C. for 18 h. The crude reaction products were purified using preparatory HPLC (Solvent A=10% MeOH-90% water-0.1% TFA, Solvent B=90% MeOH-10% water-0.1% TFA. Column: Phenomenex Luna 30×100 mm, S10, flow rate: 40 ml/min, 40-100% B, 40 min) to afford 30 mg (35% yield) of the titled compound as a yellow oil. LC-MS (M+H)+ 428.2.

Workup

  1. customThe crude reaction products
  2. customwere purified
  3. customHPLC (Solvent A=10% MeOH-90% water-0.1% TFA, Solvent B=90% MeOH-10% water-0.1% TFA. Column: Phenomenex Luna 30×100 mm, S10, flow rate: 40 ml/min, 40-100% B, 40 min)

Sources & evidence

ORD record
ord-5a44dc3ce20043afa22dfe4915219a01
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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