Toluene → HCID 24856033, compound

HRID 606008Notes

Reaction equation

HRID 606008 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[OH:18][CH2:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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.ClCCl.C(#N)C>[C:14]1([CH3:17])[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([C:24]4[CH:25]=[C:20]([CH2:19][OH:18])[CH:21]=[CH:22][CH:23]=4)=[CH:7][N:6]3[CH:8]=2)=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 14128386-bromo-2-(4-methylphenyl)imidazo[1,2-a]pyridineHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acid

Product 1

HCID 24856033HCID 24856033, compoundYield 45.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Under a stream of nitrogen, 200 mg of 6-bromo-2-p-tolylimidazo[1,2-a]pyridine, 160 mg of 3-(hydroxymethyl)phenylboronic acid and 24 mg of tetrakis(triphenylphosphine)palladium are placed in a microwave tube containing 2 ml of toluene degassed beforehand under a stream of nitrogen, 2 ml of acetonitrile and 2 ml of a 2M solution of sodium carbonate. The tube is placed in a microwave apparatus and irradiated at 150° C. for 15 min. The organic phase is separated and dried and the filtrate is concentrated under reduced pressure. The residue obtained is taken up with 6 ml of dichloromethane. The precipitate is recovered by filtration, washed with dichloromethane and dried in a desiccator under reduced pressure. 100 mg of compound are obtained. Mp=171-173° C. 1H NMR (DMSO-d6, δ in ppm): 2.32 (s, 3H); 4.57 (d, J=5.6 Hz, 2H); 5.23 (t, J=5.7 Hz, 1H); from 7.19 to 7.67 (m, 8H); 7.84 (d, J=8 Hz, 2H); 8.32 (s, 1H); 8.82 (m, 1H). M+H=315.

Workup

  1. customirradiated at 150° C. for 15 min
  2. customThe organic phase is separated
  3. customdried
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue obtained
  6. filtrationThe precipitate is recovered by filtration
  7. washwashed with dichloromethane
  8. customdried in a desiccator under reduced pressure

Sources & evidence

ORD record
ord-01b63b4a7dbc458aaf8360f5ba84c9d8
Source dataset
uspto-grants-2011_03
Patent number
US07915284B2

Reaction notes

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