Toluene → HCID 58269937, compound

HRID 472031Notes

Reaction equation

HRID 472031 reaction equation
Br[C:2]1[C:3]([CH3:13])=[C:4]2[C:11]([CH3:12])=[CH:10][NH:9][C:5]2=[C:6]([Cl:8])[N:7]=1.[CH2:14](OB(C1C=CC=CC=1)OCC)[CH3:15].[C:27]([O-])([O-])=O.[Na+].[Na+].[C:33]1([CH3:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>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>[Cl:8][C:6]1[N:7]=[C:2]([C:34]2[C:35]([CH2:14][CH3:15])=[CH:36][CH:37]=[CH:38][C:33]=2[CH2:39][CH3:27])[C:3]([CH3:13])=[C:4]2[C:11]([CH3:12])=[CH:10][NH:9][C:5]=12

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 5326085HCID 5326085, compoundHCID 58269955HCID 58269955, compound

Product 1

HCID 58269937HCID 58269937, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
86 °C

Procedure

A mixture of 5-bromo-7-chloro-3,4-dimethyl-1H-pyrrolo[2,3-c]pyridine (610 mg, 2.34 mmol), diethylphenyl boronic acid (500 mg, 2.81 mmol), Pd(PPh3)4 (140 mg, 0.12 mmol) and Na2CO3 (2M, 5 mL) in toluene (30 mL) is degassed, and stirred at 86° C. overnight. The mixture is diluted with EtOAc and washed with water and brine. The organic layer is dried over MgSO4 and concentrated under reduced pressure. Chromatography of the residue on silica gel (Hexane/EtOAc, 4:1) gives the titled compound. 1H NMR: (CDCl3) 9.10 (1H, br), 7.27 (1H, t, J=8.0 Hz), 7.14 (2H, d, J=8.0 Hz), 7.00 (1H, s), 2.46 (3H, s), 2.32 (3H, s), 2.27 (4H, q, J=7.5 Hz), 1.01 (6H, t, J=7.5 Hz).

Workup

  1. customis degassed
  2. additionThe mixture is diluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-163eaca37cfb44c3bce33b33fff3680c
Source dataset
uspto-grants-2014_01
Patent number
US08633193B2

Reaction notes

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